Comprehensive enantioselective organocatalysis catalysts, reactions, and applications

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adam_text CONTENTS FOREWORD XXVII PREFACE XXIX LIST OF CONTRIBUTORS XXXI ABBREVIATIONS XLI VOLUME 1: PRIVILEGED CATALYSTS PART I AMINO ACID-DERIVED CATALYSTS 1 1 PROLINE-RELATED SECONDARY AMINE CATALYSTS AND APPLICATIONS 3 HIYOSHIZO KOTSUKI AND NIIHA SASAKURA 1.1 INTRODUCTION 3 1.2 PROLINAMIDE AND RELATED CATALYSTS 3 1.3 PROLINAMINE AND RELATED CATALYSTS 8 1.4 PROLINE TETRAZOLE AND RELATED CATALYSTS 10 1.5 PROLINAMINE SULFONAMIDE AND RELATED CATALYSTS 13 1.6 PROLINAMINE THIOUREA AND RELATED CATALYSTS 15 1.7 MISCELLANEOUS 16 1.8 CONCLUSIONS 21 ACKNOWLEDGMENTS 21 REFERENCES 21 2 TMS-PROLINOL CATALYST IN ORGANOCATALYSIS 33 HAO JIANG, LUKASZ ALBRECHT, CUSTAV DICKMEISS, KIM L JENSEN, AND KARL ANKER JARGENSEN 2.1 INTRODUCTION 33 2.2 ENAMINE ACTIVATION 34 2.3 IMINIUM-ION ACTIVATION 37 2.4 CASCADE REACTIONS 41 2.5 DIENAMINE ACTIVATION 42 2.6 TRIENAMINE ACTIVATION 46 2.7 SUMMARY AND CONCLUSIONS 48 REFERENCES 48 HTTP://D-NB.INFO/1031647333 VI | CONTENTS 3 NON-PROLINE AMINO ACID CATALYSTS 51 LI-WEN XU AND YIXIN LU 3.1 INTRODUCTION 51 3.2 PRIMARY AMINO ACIDS IN AMINO CATALYSIS 52 3.3 PRIMARY AMINO ACID-DERIVED ORGANIC CATALYSTS 53 3.3.1 UNMODIFIED AMINO ACIDS 55 3.3.2 PROTECTED PRIMARY AMINO ACIDS 55 3.3.3 PRIMARY AMINO ACID-DERIVED DIAMINE CATALYSTS 55 3.3.4 OTHER PRIMARY AMINO ACID CATALYSTS 55 3.4 APPLICATIONS OF NON-PROLINE PRIMARY AMINO ACID CATALYSTS 56 3.4.1 ALDOL REACTION 56 3.4.2 MANNICH REACTION 60 3.4.3 MICHAEL ADDITION 62 3.4.4 OTHER REACTIONS 64 3.5 CONCLUSIONS 65 ACKNOWLEDGMENTS 66 REFERENCES 66 4 CHIRAL IMIDAZOLIDINONE (MACMILLAN S) CATALYST 69 RAINER MAHRWALD 4.1 INTRODUCTION 69 4.2 ENAMINE CATALYSIS 69 4.3 IMINIUM CATALYSIS 81 4.4 CASCADE REACTION-MERGING IMINIUM AND ENAMINE CATALYSIS 86 REFERENCES 91 5 OLIGOPEPTIDES AS MODULAR ORGANOCATALYTIC SCAFFOLDS 97 ROBERTO FANELLI AND UMBERTO PIARULLI 5.1 INTRODUCTION 97 5.2 C-C BOND FORMING REACTIONS 98 5.2.1 ALDOL REACTIONS 98 5.2.2 MICHAEL REACTIONS 101 5.2.3 MORITA-BAYLIS-HILLMAN REACTIONS 105 5.2.4 HYDROCYANATION OF ALDEHYDES 107 5.3 ASYMMETRIC ACYLATIONS 108 5.4 ASYMMETRIC PHOSPHORYLATIONS 110 5.5 ENANTIOSELECTIVE OXIDATIONS 111 5.6 HYDROLYTIC REACTIONS 114 5.7 SUMMARY AND CONCLUSIONS 114 REFERENCES 114 CONTENTS | VII PART II NON-AMINO ACID-DERIVED CATALYSTS 117 6 CINCHONAS AND CUPREIDINES 119 STEEN INGEMANN AND HENK HIEMSTRA 6.1 INTRODUCTION 119 6.2 CINCHONA ALKALOID DERIVATIVES 120 6.3 NATURAL CINCHONA ALKALOIDS, CUPREINE, AND CUPREIDINE 121 6.3.1 STRUCTURAL PROPERTIES 121 6.3.2 CATALYSIS WITH NATURAL CINCHONA ALKALOIDS 122 6.3.3 CATALYSIS WITH CUPREINE AND CUPREIDINE 125 6.4 CINCHONA ALKALOIDS WITH AN ETHER OR ESTER GROUP AT C9 127 6.4.1 STRUCTURAL PROPERTIES 127 6.4.2 CATALYSIS WITH C9 ETHERS OF NATURAL CINCHONA ALKALOIDS 127 6.4.3 CATALYSIS WITH C9 ETHERS OF CUPREINE AND CUPREIDINE 129 6.4.4 CATALYSIS WITH C9 ESTERS 133 6.5 CINCHONA ALKALOID DERIVATIVES WITH A SULFONAMIDE, UREA, THIOUREA, SQUARAMIDE, OR GUANIDINE FUNCTION 134 6.5.1 STRUCTURAL PROPERTIES 134 6.5.2 CATALYSIS WITH C9 AND C6 THIOUREA DERIVATIVES 136 6.5.3 CATALYSIS WITH C9 SULFONAMIDE, SQUARAMIDE, AND GUANIDINE DERIVATIVES 141 6.6 CINCHONA ALKALOIDS WITH A PRIMARY AMINE GROUP AT C9 145 6.6.1 STRUCTURAL PROPERTIES 145 6.6.2 CATALYSIS WITH C9 AMINO DERIVATIVES 146 6.7 CINCHONA ALKALOIDS IN PHASE-TRANSFER CATALYSIS 149 6.8 ETHER BRIDGED DIMERS 151 6.9 SOME NOVEL CINCHONA ALKALOID DERIVATIVES 153 6.10 PROSPECTS 154 REFERENCES 155 7 CHIRAL C 2 CATALYSTS 161 DAISUKE URAGUCHI, KOHSUKE OHMATSU, AND TAKASHI OOI 7.1 INTRODUCTION 161 7.2 CHIRAL LEWIS BASE CATALYSTS 161 7.2.1 PHOSPHORAMIDES 162 7.2.2 BIPYRIDINE N,N -DIOXIDES 167 7.2.3 BISPHOSPHINE DIOXIDES 169 7.3 PHOSPHINES 172 7.4 CHIRAL C 2 -SYMMETRIC SECONDARY AND PRIMARY AMINES 174 7.5 CHIRAL C 2 -SYMMETRIC BRENSTED BASES: GUANIDINES 177 7.6 CHIRAL C 2 -SYMMETRIC BRONSTED ACIDS 181 7.6.1 BINAPHTHOL AND BIPHENOL DERIVATIVES 181 7.6.2 PYRIDINIUM DISULFONATES 182 7.6.3 DICARBOXYLIC ACIDS 183 7.6.4 CHIRAL DISULFONIMIDES 186 VIII | CONTENTS 7.7 CHIRAL C 2 -SYMMETRIC BIS-THIOUREAS 188 7.8 CHIRAL C 2 -SYMMETRIC AMINOPHOSPHONIUM IONS 189 7.9 SUMMARY AND CONCLUSIONS 190 REFERENCES 190 8 PLANAR CHIRAL CATALYSTS 195 OLIVIER R. P. DAVID 8.1 INTRODUCTION 195 8.2 LEWIS/BRANSTED BASES 198 8.2.1 NITROGEN BASES 198 8.2.1.1 AZAFERROCENES 199 8.2.1.2 PYRIDINOFERROCENES 200 8.2.1.3 IMIDAZOLES 204 8.2.1.4 PIP: PARACYCLOPHANE-2,3-DIHYDROIMIDAZOLO[L,2-A]PYRIDINE BASES 204 8.2.1.5 IMINE 205 8.2.2 OXYGEN LEWIS BASES 206 8.2.3 PHOSPHINE 207 8.2.4 N-HETEROCYDIC CARBENES 209 8.2.5 SULFIDES 210 8.3 LEWIS/BRANSTED ACIDS 211 8.3.1 BORONIC ACIDS 211 8.3.2 PHENOLS 212 8.3.3 THIOUREAS 212 8.4 REDOX REACTIONS 213 8.4.1 FLAVIN DERIVATIVES 213 8.4.2 HANTZSCH ESTERS 214 8.5 SUMMARY AND CONCLUSIONS 214 REFERENCES 215 9 DYNAMIC APPROACHES TOWARDS CATALYST DISCOVERY 221 PATRIZIA GALZERANO, CIULIO GASPARINI, MARTA DAL MOLIN, AND LEONARD J. PRINS 9.1 INTRODUCTION 221 9.2 SELF-ASSEMBLY 222 9.2.1 SELF-ASSEMBLED ORGANOCATALYSTS 223 9.2.2 CATALYSIS IN CONFINED SELF-ASSEMBLED SPACE 227 9.3 SELF-SELECTED CATALYSTS 232 9.3.1 DYNAMIC COMBINATORIAL CHEMISTRY 232 9.4 CONCLUSIONS 236 ACKNOWLEDGMENTS 236 REFERENCES 236 APPENDIX A1 CONTENTS IIX VOLUME 2: ACTIVATIONS PART I ASYMMETRIC CATALYSIS WITH NON-COVALENT INTERACTIONS 239 10 BRANSTED ACIDS 241 YUNUS E. TURKMEN, YE ZHU, AND VIRESH H. RAWAL 10.1 INTRODUCTION 241 10.2 CHIRAL ALCOHOL CATALYSTS 245 10.3 CHIRAL SQUARAMIDES AS HYDROGEN-BOND DONOR CATALYSTS 252 10.3.1 INTRODUCTION 252 10.3.1.1 MICHAEL ADDITION REACTION INVOLVING NITROALKENES 253 10.3.1.2 MICHAEL ADDITION REACTION INVOLVING TRCMS-CHALCONES 257 10.3.1.3 MICHAEL ADDITION REACTION INVOLVING OTHER C=C MICHAEL ACCEPTORS 259 10.3.1.4 REACTIONS INVOLVING A C=N BOND 261 10.3.1.5 REACTIONS INVOLVING A C=0 BOND 261 10.3.1.6 REACTIONS INVOLVING A N=N BOND 263 10.3.1.7 DYNAMIC KINETIC RESOLUTION AND DESYMMETRIZATION 263 10.3.1.8 CASCADE REACTIONS 266 10.3.2 SUMMARY AND OUTLOOK 268 10.4 GUANIDINES/GUANIDINIUMS 269 10.5 MISCELLANEOUS BRANSTED ACIDS 275 10.5.1 AMINOPYRIDINIUMS 275 10.5.2 TETRAAMINOPHOSPHONIUMS 278 10.5.3 AXIALLY CHIRAL DICARBOXYLIC ACIDS 280 10.5.4 STRONGER BRANSTED ACIDS 282 10.6 ADDENDUM 282 REFERENCES 282 11 BRANSTED ACIDS: CHIRAL PHOSPHORIC ACID CATALYSTS IN ASYMMETRIC SYNTHESIS 289 KEIJI MORI AND TAKAHIKO AKIYAMA 11.1 INTRODUCTION 289 11.1.1 DESIGN OF CHIRAL PHOSPHORIC ACIDS 289 11.2 REACTION WITH IMINES 291 11.2.1 MANNICH REACTION 291 11.2.2 HYDROPHOSPHONYLATION 293 11.2.3 CYCLOADDITION REACTION 295 11.2.4 TRANSFER HYDROGENATION 297 11.3 FRIEDEL-CRAFTS REACTION 304 11.4 INTRAMOLECULAR ALDOL REACTION 309 11.5 RING OPENING OF MESO-AZIRIDINES 311 11.6 FUTURE PROSPECTS 312 REFERENCES 312 X | CONTENTS 12 BRENSTED ACIDS: CHIRAL (THIO)UREA DERIVATIVES 315 CERGELY JAKAB AND PETER R. SCHREINER 12.1 INTRODUCTION 315 12.1.1 EXPLICIT DOUBLE HYDROGEN-BONDING INTERACTIONS 315 12.1.2 THE BEGINNINGS OF (THIO)UREA CATALYSIS 316 12.2 IMPORTANT CHIRAL (THIO)UREA ORGANOCATALYSTS 318 12.2.1 TAKEMOTO S CATALYST 318 12.2.2 CINCHONA ALKALOIDS IN (THIO)UREA ORGANOCATALYSIS 322 12.2.3 PYRROLIDINE-(THIO)UREA CATALYSIS 325 12.2.4 NAGASAWA S CATALYST 326 12.2.5 RICCI S THIOUREA CATALYST 328 12.2.6 BINAPHTHYLAMINE SCAFFOLDS IN (THIO)UREA CATALYSIS 329 12.2.7 JACOBSEN S CATALYST FAMILY 330 12.2.8 N-SULFINYL (THIO)UREA CATALYSTS 335 12.3 SUMMARY 336 REFERENCES 336 13 BRENSTED BASES 343 AMAL TING AND SCOTT E. SCHAUS 13.1 INTRODUCTION 343 13.2 CINCHONA ALKALOIDS 344 13.2.1 CINCHONA ALKALOIDS IN ASYMMETRIC TRANSFORMATIONS 345 13.2.2 ASYMMETRIC ACTIVATION OF CONJUGATE ADDITION TO ENONES 346 13.2.3 ASYMMETRIC ACTIVATION OF CONJUGATE ADDITION TO IMINES 347 13.2.4 ASYMMETRIC AMINATIONS 349 13.2.5 ASYMMETRIC ACTIVATION OF ISOCYANOACETATES 350 13.2.6 ASYMMETRIC DIELS-ALDER REACTION 351 13.3 BRENSTED BASE-DERIVED THIOUREA CATALYSTS 352 13.3.1 ASYMMETRIC CONJUGATE ADDITION WITH CARBONYLS AND IMINES 353 13.3.2 ASYMMETRIC CONJUGATE ADDITIONS WITH NON-TRADITIONAL SUBSTRATES 354 13.3.2.1 ASYMMETRIC CASCADE REACTIONS 356 13.4 CHIRAL GUANIDINE CATALYSTS 356 13.4.1 ASYMMETRIC CONJUGATE ADDITION TO ENONES AND IMINES 357 13.4.2 ASYMMETRIC DIELS-ALDER REACTIONS 360 13.5 CONCLUSION 361 REFERENCES 362 14 CHIRAL ONIUM SALTS (PHASE-TRANSFER REACTIONS) 365 SEIJI SHIRAKAWA AND KEIJI MARUOKA 14.1 INTRODUCTION 365 14.2 PHASE-TRANSFER CATALYSIS 366 14.2.1 PHASE-TRANSFER REACTION OF ACTIVE METHYLENE OR METHINE COMPOUNDS WITH INORGANIC BASE 366 14.2.1.1 GENERATION OF ONIUM CARBANION 366 14.2.1.2 NUCLEOPHILIC SUBSTITUTION 367 CONTENTS | XI 14.2.1.3 NUDEOPHILIC ADDITION 368 14.2.2 PHASE-TRANSFER CATALYZED ADDITION OF ANION SUPPLIED AS METAL SALT 370 14.2.3 BASE-FREE NEUTRAL PHASE-TRANSFER REACTION 371 14.3 ONIUM FLUORIDES 372 14.4 ONIUM PHENOXIDES AND RELATED COMPOUNDS 374 14.4.1 ONIUM PHENOXIDES AS LEWIS BASE CATALYSTS 375 14.4.2 ONIUM PHENOXIDES AND RELATED COMPOUNDS AS BRANSTED BASE CATALYSTS 375 14.5 CONCLUSIONS 377 REFERENCES 377 15 LEWIS BASES 381 PAVEL KOIOVSKY AND ANDREI V. MALKOV 15.1 INTRODUCTION 381 15.2 ALLYLATION REACTIONS 382 15.2.1 CATALYTIC ALLYLATION OF ALDEHYDES 382 15.2.2 STOICHIOMETRIC ALLYLATION OF ALDEHYDES AND KETONES 393 15.3 PROPARGYLATION, ALLENYLATION, AND ADDITION OF ACETYLENES 395 15.3.1 ADDITION TO ALDEHYDES 395 15.3.2 ADDITION TO IMINES 395 15.4 ALDOL-TYPE REACTIONS 396 15.5 CYANATION AND ISONITRILE ADDITION 404 15.5.1 CYANATION OF ALDEHYDES 404 15.5.2 CYANATION OF IMINES (STRECKER REACTION) 407 15.6 REDUCTION REACTIONS 408 15.7 EPOXIDE OPENING 417 15.8 CONCLUSION AND OUTLOOK 421 REFERENCES 421 16 LEWIS ACIDS 431 TATJANA HECKEL AND RENT V/ILHELM 16.1 INTRODUCTION 431 16.2 SILYL CATION BASED CATALYSTS 433 16.3 HYPERVALENT SILICON BASED CATALYSTS 438 16.4 PHOSPHONIUM CATION BASED CATALYSTS 444 16.5 CARBOCATION BASED CATALYSTS 448 16.6 IONIC LIQUIDS 455 16.7 MISCELLANEOUS CATALYSTS 458 16.8 CONCLUSION 459 REFERENCES 459 XIII CONTENTS PART II ASYMMETRIC CATALYSIS WITH COVALENT INTERACTIONS 463 17 RATIONALIZING REACTIVITY AND SELECTIVITY IN AMINOCATALYTIC REACTIONS 465 RAGHAVAN B. SUNOJ 17.1 INTRODUCTION 465 17.2 SECONDARY AMINE CATALYSIS 466 17.2.1 MECHANISM OF SECONDARY AMINE CATALYSIS 466 17.2.1.1 IMPORTANT INTERMEDIATES IN AMINO CATALYSIS 467 17.2.1.2 EXPERIMENTAL IDENTIFICATION OF ENAMINES IN ORGANOCATALYSIS 469 17.2.1.3 ENAMINE RADICAL CATION: THE CONCEPT OF SOMO ACTIVATION 471 17.3 STEREOSELECTIVITY IN PROLINE-CATALYZED REACTIONS 472 17.3.1 TRANSITION STATE MODELS FOR PROLINE-CATALYZED REACTIONS 473 17.3.2 LIMITATIONS OF HYDROGEN-BONDING GUIDED TRANSITION STATE MODELS 475 17.4 MECHANISM AND STEREOSELECTIVITY IN ORGANOCATALYTIC CASCADE REACTIONS 482 17.4.1 STEREOSELECTIVITY IN OTHER AMINO ACID CATALYZED REACTIONS 485 17.5 RATIONAL DESIGN OF CATALYSTS 486 17.6 SUMMARY AND CONCLUSIONS 491 ACKNOWLEDGMENTS 492 REFERENCES 492 18 CARBENE CATALYSTS 495 KAREN THAI, EDUARDO SDNCHEZ-LARIOS, AND MICHEL GRAVEL 18.1 INTRODUCTION 495 18.2 REACTIONS OF ACYL ANION EQUIVALENTS 497 18.2.1 BENZOIN REACTION 497 18.2.1.1 HOMO-BENZOIN REACTION 497 18.2.1.2 CROSS-BENZOIN REACTION 498 18.2.1.3 AZA-BENZOIN REACTION 501 18.2.2 STETTER REACTION 501 18.2.2.1 INTRAMOLECULAR STETTER REACTIONS 501 18.2.2.2 INTERMOLECULAR STETTER REACTIONS 503 18.2.2.3 APPLICATION OF STETTER REACTIONS TO NATURAL PRODUCT SYNTHESIS 505 18.2.3 HYDROACYLATION REACTIONS 505 18.3 EXTENDED UMPOLUNG 506 18.3.1 REACTIONS OF A-REDUCIBLE ALDEHYDES 506 18.3.2 REACTIONS OF ENALS AND YNALS 508 18.3.2.1 C-C BOND FORMING REACTIONS AT THE P POSITION 508 18.3.2.2 P-PROTONATION OF HOMOENOLATES 511 18.3.2.3 OXIDATION OF ENALS 513 18.4 UMPOLUNG OF ACTIVATED OLEFINS 514 18.5 NUCLEOPHILIC CATALYSIS 515 18.6 CONCLUSION 518 REFERENCES 518 CONTENTS XIII 19 OXIDES AND EPOXIDES 523 HARRY J. MILNER AND ALAN ARMSTRONG 19.1 ALKENE EPOXIDATION 523 19.1.1 KETONE-MEDIATED EPOXIDATION 524 19.1.2 IMINIUM SALT-CATALYZED EPOXIDATION 532 19.1.3 ASPARTATE-DERIVED PERACID CATALYSIS 536 19.2 HYPERVALENT IODINE-CATALYZED OXIDATIONS 537 19.2.1 ASYMMETRICAL NAPHTHOL DEAROMATIZATION 537 19.2.2 ENANTIOSELECTIVE A-OXYSULFONYLATION OF KETONES 538 19.3 OXIDATION OF THIOETHERS AND DISULFIDES 539 19.4 RESOLUTION OF ALCOHOLS BY OXIDATION 540 REFERENCES 542 20 YLIDES 547 SAIHU LIAO, PENG WANG, AND YONG TANG 20.1 INTRODUCTION 547 20.2 ENANTIOSELECTIVE SULFUR YLIDE CATALYSIS 548 20.2.1 EPOXIDATION 549 20.2.1.1 CATALYSIS VIA SULFIDE ALKYLATION/DEPROTONATION 549 20.2.1.2 CATALYSIS VIA TRANSITION METAL-MEDIATED CARBENE TRANSFER TO SULFIDES 556 20.2.2 AZIRIDINATION 560 20.2.3 CYDOPROPANATION 562 20.3 ENANTIOSELECTIVE PHOSPHORUS AND ARSENIC YLIDE CATALYSIS 566 20.4 ENANTIOSELECTIVE NITROGEN YLIDE CATALYSIS 570 20.5 ENANTIOSELECTIVE SELENIUM AND TELLURIUM YLIDE CATALYSIS 573 20.6 SUMMARY AND CONCLUSIONS 574 REFERENCES 575 PART III TUNING CATALYST ACTIVITY AND SELECTIVITY BY THE REACTION MEDIUM AND CONDITIONS 579 21 NON-CLASSICAL ACTIVATION OF ORGANOCATALYTIC REACTIONS (PRESSURE, MICROWAVE IRRADIATION.) 581 PIOTR KWIATKOWSKI, KRZYSZTOF DUDZIHSKI, AND DAWID LYZWA 21.1 INTRODUCTION 581 21.2 ASYMMETRIC ORGANOCATALYSIS UNDER HIGH-PRESSURE CONDITIONS 581 21.3 ASYMMETRIC ORGANOCATALYSIS UNDER MICROWAVE IRRADIATION-THERMAL EFFECT 593 21.4 ASYMMETRIC ORGANOCATALYSIS UNDER ULTRASOUND IRRADIATION 601 21.5 ASYMMETRIC ORGANOCATALYSIS UNDER BALL MILLING CONDITIONS 605 21.6 SUMMARY AND CONCLUSIONS 612 REFERENCES 613 XIV | CONTENTS 22 IONIC LIQUID ORGANOCATALYSTS 617 DMITRY E. SIYUTKIN, ALEXANDER S. KUCHERENKO, AND SERGEI G. ZLOTIN 22.1 INTRODUCTION 617 22.2 IONIC LIQUIDS AS RECYCLABLE SOLVENTS FOR ASYMMETRIC ORGANOCATALYTIC REACTIONS 618 22.2.1 A-AMINO ACID-PROMOTED REACTIONS IN IL MEDIA 618 22.2.2 REACTIONS IN THE PRESENCE OF OTHER CHIRAL ORGANOCATALYSTS IN IL MEDIA 623 22.3 NON-SOLVENT APPLICATIONS OF IONIC LIQUIDS AND THEIR CONGENERS IN ASYMMETRIC ORGANOCATALYSIS 625 22.3.1 IMMOBILIZATION OF ORGANOCATALYSTS THROUGH ELECTROSTATIC INTERACTION WITH IONIC FRAGMENTS 626 22.3.1.1 BIPHASIC NON-COVALENT IMMOBILIZATION ON IONIC LIQUIDS AND IONIC POLYMERS 626 22.3.1.2 ION-PAIR IMMOBILIZATION ON IONIC LIQUIDS 628 22.3.2 MODIFICATION OF ORGANOCATALYSTS BY IONIC GROUPS THROUGH COVALENT BONDING 630 22.3.2.1 IONIC ORGANOCATALYSTS INCORPORATING A-AMINO ACID UNITS 631 22.3.2.2 IONIC ORGANOCATALYSTS INCORPORATING A-AMINO AMIDE UNITS 636 22.3.2.3 PYRROLIDINE-SOURCED IONIC ORGANOCATALYSTS 638 22.3.2.4 OTHER ORGANOCATALYSTS BEARING IONIC GROUPS 644 22.4 CONCLUSION 646 REFERENCES 647 23 POLYMER AND MESOPOROUS MATERIAL SUPPORTED ORGANOCATALYSTS 651 TOR ERIK KRISTENSEN AND TORE HANSEN 23.1 INTRODUCTION 651 23.2 POLYMER-SUPPORTED ORGANOCATALYSTS 652 23.2.1 POLYMER RESINS FOR IMMOBILIZATION OF CHIRAL ORGANOCATALYSTS 652 23.2.2 POLYMER-SUPPORTED CINCHONA DERIVATIVES 653 23.2.3 POLYMER-SUPPORTED ENAMINE-IMINIUM ORGANOCATALYSTS 656 23.2.4 MISCELLANEOUS POLYMER-SUPPORTED CHIRAL ORGANOCATALYSTS 662 23.3 MESOPOROUS-SUPPORTED ORGANOCATALYSTS 663 23.3.1 MESOPOROUS MATERIALS FOR IMMOBILIZATION OF CHIRAL ORGANOCATALYSTS 663 23.3.2 INORGANIC AND INORGANIC-ORGANIC HYBRID MATERIAL SUPPORTED CHIRAL ORGANOCATALYSTS 664 23.4 CONCLUSIONS AND OUTLOOK 668 REFERENCES 668 24 WATER IN ORGANOCATALYTIC REACTIONS 673 FRANCESCO CIACALONE AND MICHELANGELO CRUTTADAURIA 24.1 INTRODUCTION 673 24.2 ALDOL REACTIONS 678 24.2.1 PRIMARY AMINES 678 CONTENTS I XV 24.2.2 SECONDARY AMINES 682 24.2.3 PROLINES SUBSTITUTED AT THE 4-POSITION 683 24.2.4 PROLINAMIDES 687 24.2.5 SUPPORTED PROLINE AND PROLINE DERIVATIVES 694 24.3 MICHAEL REACTIONS 696 24.4 MANNICH REACTION 705 24.5 DIELS-ALDER REACTION 707 24.6 MISCELLANEOUS EXAMPLES 710 REFERENCES 713 VOLUME 3: REACTIONS AND APPLICATIONS PART I ALPHA-ALKYLATION AND HETEROATOM FUNCTIONALIZATION 719 25 S N 2-TYPE ALPHA-ALKYLATION AND ALLYLATION REACTIONS 721 CHRISTINE TRAN AND PETER I. DALKO 25.1 S N 2-TYPE ALKYLATION UNDER HOMOGENOUS CONDITIONS 721 25.2 DOMINO REACTIONS INCLUDING S N 2-TYPE ALKYLATIONS 722 25.2.1 MICHAEL/S N 2 REACTIONS WITH THE HALIDE ON THE DONOR 723 25.2.2 MICHAEL/S N 2 REACTIONS WITH THE HALIDE ON THE ACCEPTOR 724 25.3 INTERMOLECULAR S N 2 ALKYLATIONS UNDER HOMOGENOUS CONDITIONS 726 25.4 SUMMARY 727 REFERENCES 727 26 ALPHA-ALKYLATION BY S N 1-TYPE REACTIONS 729 ANDREA GUALANDI, DIEGO PETRUZZIELLO, ENRICO EMER, AND PIER GIORGIO COZZI 26.1 INTRODUCTION 729 26.2 S N .1-TYPE NUCLEOPHILIC REACTION BY GENERATION OF CARBOCATIONS 730 26.3 ORGANOCATALYTIC STEREOSELECTIVE S N 1-TYPE REACTIONS WITH ENAMINE CATALYSIS 733 26.4 ASYMMETRIC S N 1-TYPE A-ALKYLATION OF KETONES 737 26.5 COMBINATION OF ENAMINE CATALYSIS AND LEWIS ACIDS IN S N .1-TYPE REACTIONS 738 26.6 ORGANOCATALYTIC S N 1-TYPE REACTIONS WITH BRANSTED ACIDS 741 26.6.1 ORGANOCATALYTIC S N 1-TYPE REACTIONS WITH BRANSTED ACIDS AND METALS 746 26.7 S N 1-TYPE REACTION PROMOTED BY CHIRAL THIOUREAS 747 26.8 S N 1-TYPE ORGANOCATALYTIC REACTION OF IMINIUM, OXONIUM, AND AZIRIDINIUM INTERMEDIATES 749 26.9 CONCLUSIONS AND PERSPECTIVES 751 REFERENCES 751 CONTENTS 27 ALPHA-HETEROATOM FUNATIONALIZATION OF CARBONYL COMPOUNDS 757 GABRIELA CUILLENA 27.1 INTRODUCTION 757 27.2 ENANTIOSELECTIVE A-PNICTOGENATION OF CARBONYL COMPOUNDS 758 27.2.1 AMINATION OF CARBONYL COMPOUNDS 758 27.2.1.1 AZIRIDINATION OF A,(J-UNSATURATED CARBONYL COMPOUNDS 758 27.2.1.2 DIRECT A-AMINATION 761 27.2.2 PHOSPHINATION OF CARBONYL COMPOUNDS 769 27.3 ENANTIOSELECTIVE A-CHALCOGENATION 770 27.3.1 C-0 FORMATION 770 27.3.1.1 DARZENS REACTION 770 27.3.1.2 EPOXIDATION OF A,F}-UNSATURATED CARBONYL COMPOUNDS 771 27.3.1.3 AMINOXYLATION OF CARBONYL COMPOUNDS 774 27.3.1.4 MISCELLANEOUS OXIDATION PROCESSES 777 27.3.2 SULFENYLATION AND SELENENYLATION PROCESSES 778 27.4 ENANTIOSELECTIVE A-HALOGENATION OF CARBONYL COMPOUNDS 779 27.5 SUMMARY AND CONCLUSIONS 783 REFERENCES 783 PART II NUDEOPHILE ADDITION TO C=X BONDS 791 28 ALDOL AND MANNICH-TYPE REACTIONS 793 NOBUYUKI MASE AND CARLOS F. BARBAS III 28.1 INTRODUCTION 793 28.2 ENAMINE CATALYSIS 795 28.2.1 ALDOL REACTIONS IN ENAMINE CATALYSIS 796 28.2.1.1 INTERMOLECULAR ALDOL REACTIONS IN ENAMINE CATALYSIS 796 28.2.1.2 INTRAMOLECULAR ALDOL REACTIONS USING ENAMINE CATALYSIS 799 28.2.1.3 ALDOL REACTIONS IN WATER, ON WATER, AND BY WATER 801 28.2.1.4 METAL-CATALYZED AND ORGANOCATALYTIC REACTION SEQUENCES 805 28.2.1.5 ORGANOCATALYTIC AND BIOCATALYTIC REACTION SEQUENCES 805 28.2.2 MANNICH REACTIONS IN ENAMINE CATALYSIS 806 28.2.2.1 ANTI-SELECTIVE MANNICH REACTIONS 806 28.2.2.2 MANNICH REACTIONS OF ACETALDEHYDE DONORS 809 28.3 BRANSTED ACID CATALYSIS INCLUDING HYDROGEN-BOND CATALYSIS 810 28.3.1 ALDOL REACTIONS IN BRANSTED ACID AND HYDROGEN-BOND CATALYSIS 811 28.3.1.1 INTERMOLECULAR ALDOL REACTIONS IN BRANSTED ACID AND HYDROGEN-BOND CATALYSIS 811 28.3.1.2 INTRAMOLECULAR ALDOL REACTIONS IN BRANSTED ACID CATALYSIS 814 28.3.2 MANNICH REACTIONS WITH BRANSTED ACID AND HYDROGEN-BOND CATALYSIS 815 28.3.2.1 VINYLOGOUS MUKAIYAMA MANNICH REACTIONS WITH BRANSTED ACID CATALYSIS 815 28.3.2.2 MANNICH-TYPE REACTIONS OF ENECARBAMATES WITH BRANSTED ACID CATALYSIS 816 CONTENTS | XVII 28.3.2.3 MANNICH REACTIONS CATALYZED BY CHIRAL CALCIUM PHOSPHATE 817 28.4 BRONSTED BASE CATALYSIS INCLUDING BIFUNCTIONAL CATALYSIS 817 28.4.1 ALDOL REACTIONS IN BRONSTED BASE CATALYSIS INCLUDING BIFUNCTIONAL CATALYSIS 818 28.4.1.1 VINYLOGOUS ALDOL REACTIONS IN BRONSTED BASE CATALYSIS 818 28.4.1.2 NITROALDOL (HENRY) REACTIONS WITH BRONSTED BASE CATALYSIS 818 28.4.1.3 BRONSTED BASE CATALYZED ALDOL REACTIONS OF ISATINS 819 28.4.1.4 BRONSTED BASE CATALYZED ALDOL REACTION OF 5 H-OXAZOL-4-ONES 821 28.4.2 MANNICH REACTIONS IN BRONSTED BASE CATALYSIS INCLUDING BIFUNCTIONAL CATALYSIS 822 28.4.2.1 SOLVENT-DEPENDENT GUANIDINE BASE CATALYZED MANNICH REACTIONS 822 28.4.2.2 CHIRAL AMMONIUM BETAINE-CATALYZED MANNICH REACTIONS 822 28.4.2.3 QUATERNARY PHOSPHONIUM SALT-CATALYZED MANNICH REACTIONS 823 28.5 PHASE-TRANSFER CATALYSIS 824 28.5.1 ALDOL REACTIONS IN PHASE-TRANSFER CATALYSIS 824 28.5.1.1 AXIALLY CHIRAL QUATERNARY AMMONIUM SALT-CATALYZED ALDOL REACTIONS 824 28.5.1.2 GUANIDINIUM-THIOUREA-CATALYZED NITROALDOL REACTIONS 825 28.5.2 MANNICH REACTIONS IN PHASE-TRANSFER CATALYSIS 826 28.5.2.1 QUATERNARY AMMONIUM SALT-CATALYZED MANNICH REACTIONS 826 28.5.2.2 GUANIDINIUM-THIOUREA-CATALYZED MANNICH REACTIONS 827 28.5.2.3 QUATERNARY PHOSPHONIUM SALT-CATALYZED MANNICH REACTIONS 828 28.5.3 QUATERNARY AMMONIUM SALT-CATALYZED 6IR ELECTROCYCLIZATION 829 28.6 N-HETEROCYDIC CARBENE (NHC) CATALYSIS 829 28.6.1 NHC-CATALYZED MANNICH-TYPE REACTIONS 829 28.7 SUPPORTED ORGANOCATALYSIS 831 28.7.1 COVALENTLY SUPPORTED ORGANOCATALYSTS 831 28.7.1.1 MAGNETICALLY SUPPORTED ORGANOCATALYSTS 831 28.7.2 NON-COVALENTLY SUPPORTED ORGANOCATALYSTS 832 28.7.2.1 POLYOXOMETALATE-SUPPORTED ORGANOCATALYSTS 832 28.7.2.2 CLAY-SUPPORTED ORGANOCATALYSTS 832 28.7.3 SUPPORTED ORGANOCATALYSTS IN MULTIPHASIC SYSTEMS 834 28.7.3.1 TAGGED ORGANOCATALYSTS 834 28.7.3.2 SUPPORTED IONIC LIQUID PHASE CATALYSIS 834 28.8 SUMMARY AND CONCLUSIONS 835 REFERENCES 835 29 ADDITIONS OF NITROALKYLS AND SULFONES TO C=X 841 AITOR LANCIA, ROSA LDPEZ, MIKE! OIARBIDE, AND CLAUDIO PALOMO 29.1 ORGANOCATALYTIC ADDITION OF NITROALKANES TO C=0 (THE HENRY REACTION) 841 29.1.1 ORGANOCATALYTIC ADDITION OF NITROALKANES TO ALDEHYDES 841 29.1.2 ORGANOCATALYTIC ADDITION OF NITROALKANES TO KETONES 846 29.2 ADDITION OF NITROALKANES TO C=NR (THE AZA-HENRY OR NITRO-MANNICH REACTION) 851 XVIII CONTENTS 29.2.1 BRANSTED BASE CATALYZED AZA-HENRY REACTIONS 852 29.2.2 HYDROGEN BOND CATALYZED AZA-HENRY REACTIONS 857 29.2.3 PHASE-TRANSFER CONDITIONS (PTC) 862 29.2.4 MISCELLANEOUS 864 29.3 ORGANOCATALYTIC ADDITION OF SULFONES TO C=X 864 29.3.1 INTRODUCTION 864 29.3.2 ORGANOCATALYTIC ADDITION OF SULFONES TO C=0 864 29.3.3 ORGANOCATALYTIC ADDITION OF SULFONES TO C=N 865 29.4 SUMMARY AND OUTLOOK 868 REFERENCES 868 30 HYDROCYANATION AND STRECKER REACTIONS 873 CARSTEN KRAMER AND STEFAN BRASE 30.1 INTRODUCTION 873 30.1.1 OVERVIEW 873 30.2 AMINO-ACID CONTAINING CATALYSTS FOR CARBONYL HYDROCYANATION 873 30.3 THIOUREA CATALYSTS FOR CARBONYL HYDROCYANATION 875 30.4 C 2 -SYMMETRICAL GUANIDINES AND N,N -DIOXIDES 876 30.5 DIKETOPIPERAZINES AS CATALYSTS FOR THE STRECKER REACTION 877 30.6 (THIO)UREA CATALYSTS FOR THE STRECKER REACTION 878 30.7 GUANIDINES AS CATALYSTS FOR THE STRECKER REACTION 886 30.8 N,N -DIOXIDES AND BIS-FORMAMIDES AS CATALYSTS FOR THE STRECKER REACTION 886 30.9 CHIRAL QUATERNARY AMMONIUM SALTS AS CATALYSTS FOR THE STRECKER REACTION 890 30.10 BINOL-PHOSPHATES AS CATALYSTS FOR THE STRECKER REACTION 893 30.11 OTHER CATALYSTS FOR THE STRECKER REACTION 895 REFERENCES 896 31 THE MORITA-BAYLIS-HILLMAN (MBH) AND HETERO-MBH REACTIONS 899 YIN WEI AND MIN SHI 31.1 INTRODUCTION 899 31.2 RECENT MECHANISTIC INSIGHTS INTO THE MBH/AZA-MBH REACTION AND ITS ASYMMETRIC VERSION 900 31.2.1 AMINE CATALYZED MECHANISM 900 31.2.2 PHOSPHINE CATALYZED MECHANISM 905 31.2.3 MECHANISTIC INSIGHTS INTO THE MBH/AZA-MBH REACTION USING CO-CATALYTIC SYSTEMS OR MULTI-/BIFUNCTIONAL CATALYSTS 906 31.2.4 STEREOSELECTIVITY OF THE MBH/AZA-MBH REACTION 908 31.3 RECENT DEVELOPMENTS OF ESSENTIAL COMPONENTS 910 31.4 RECENT DEVELOPMENTS OF ASYMMETRIC MBH/AZA-MBH REACTIONS 914 31.4.1 ASYMMETRIC INDUCTION WITH SUBSTRATES 914 31.4.2 CATALYTIC ASYMMETRIC INDUCTION WITH CHIRAL LEWIS BASES 916 31.4.2.1 CHIRAL TERTIARY AMINE CATALYSTS 916 CONTENTS 31.4.2.2 CHIRAL TERTIARY PHOSPHINE CATALYSTS 31.4.3 CATALYTIC ASYMMETRIC INDUCTION WITH 31.4.4 CATALYTIC ASYMMETRIC INDUCTION WITH 31.4.4.1 CATALYTIC ASYMMETRIC INDUCTION WITH 31.4.4.2 CATALYTIC ASYMMETRIC INDUCTION WITH 31.4.4.3 CATALYTIC ASYMMETRIC INDUCTION WITH 31.5 CONCLUSIONS 937 REFERENCES 938 32 REDUCTION OF C=0 AND C=N 941 CUILONG LI AND JON C. ANTILLA 32.1 INTRODUCTION 941 32.2 HANTZSCH ESTER AS THE HYDRIDE SOURCE 941 32.2.1 REDUCTION OF C=N BONDS IN ACYCLIC SYSTEMS 942 32.2.2 REDUCTION OF C=N BONDS IN CYCLIC SUBSTRATES 947 32.2.2.1 REDUCTION OF C=N BONDS IN HETEROARENES 947 32.2.2.2 REDUCTION OF CYCLIC IMINES 948 32.2.3 TRANSFER HYDROGENATION COMBINED WITH OTHER TRANSFORMATIONS 951 32.2.4 IMMOBILIZED CHIRAL CATALYSTS FOR C=N BOND REDUCTION 953 32.2.5 MECHANISTIC CONSIDERATION 954 32.3 TRICHLOROSILANE AS THE REDUCING REAGENT 955 32.3.1 ASYMMETRIC REDUCTION OF KETIMINES 955 32.3.2 REDUCTION OF ENAMINES 960 32.3.3 REDUCTION OF C=N BONDS CATALYZED BY RECOVERABLE LEWIS BASE CATALYSTS 962 32.3.4 ASYMMETRIC REDUCTION OF C=0 BONDS 963 32.4 OTHER HYDROGEN SOURCES 964 32.4.1 BENZOTHIAZOLINES 964 32.4.2 BORANES 966 32.4.3 HYDROGEN AS THE SOURCE? 967 32.4.3.1 CHIRAL FRUSTRATED LEWIS PAIRS AS CATALYSTS 967 32.4.3.2 H 2 AS A TERMINAL HYDROGEN SOURCE: COMBINED HYDROGENATION BY ORGANOCATALYSIS AND METAL CATALYSIS 969 32.5 SUMMARY AND CONCLUSIONS 971 REFERENCES 971 PART III NUDEOPHILE ADDITION TO C=C BONDS 975 33 ADDITION TO OT,F)-UNSATURATED ALDEHYDES AND KETONES 977 RAMON RIOS AND XAVIER COMPANYD 33.1 INTRODUCTION 977 33.1.1 IMINIUM ACTIVATION 978 33.1.1.1 HISTORICAL OVERVIEW 978 33.2 NUDEOPHILIC ADDITION TO ENALS AND KETONES 979 33.2.1 IMINIUM ACTIVATION 979 922 CHIRAL LEWIS ACIDS 929 CHIRAL BRANSTED ACIDS 930 CHIRAL THIOUREAS 930 PROLINE DERIVATIVES 933 CHIRAL THIOLS 936 XX | CONTENTS 33.2.1.1 CATALYZED BY SECONDARY AMINES 980 33.2.1.2 PRIMARY AMINE CATALYSIS 982 33.2.1.3 ACDC CATALYSTS 982 33.2.2 SCOPE OF THE NUDEOPHILIC ADDITION TO ENALS 983 33.2.2.1 C-C BOND FORMATION 983 33.2.2.2 C-N BOND FORMATION 989 33.2.2.3 C-O BOND FORMATION 993 33.2.2.4 C-S BOND FORMATION 994 33.2.2.5 C-P BOND FORMATION 994 33.2.2.6 C-H BOND FORMATION 996 33.2.3 SCOPE OF THE NUDEOPHILIC ADDITION TO A,P-UNSATURATED KETONES 997 33.2.3.1 C-C BOND FORMATION 997 33.2.3.2 C-N BOND FORMATION 1003 33.2.3.3 C-O BOND FORMATION 1004 33.2.3.4 C-S BOND FORMATION 1005 33.2.3.5 OTHER MICHAEL REACTIONS 1006 33.3 CONCLUSION 1008 REFERENCES 1008 34 ADDITION TO NITROOLEFINS AND VINYL SULFONES 1013 CHRISTILE ROUX AND CYRIL BRESSY 34.1 INTRODUCTION 1013 34.2 ADDITION TO NITROOLEFINS 1013 34.2.1 ENAMINE ACTIVATION 1013 34.2.1.1 SECONDARY AMINES 1013 34.2.1.2 PRIMARY AMINES-ANTI-SELECTIVITY 1015 34.2.1.3 APPLICATIONS IN TOTAL SYNTHESIS 1018 34.2.2 HYDROGEN BONDING ACTIVATION 1019 34.2.2.1 CARBON-CENTERED NUCLEOPHILES 1019 34.2.2.2 OXA-MICHAEL ADDITION 1021 34.2.2.3 SULFA-MICHAEL ADDITION 1023 34.2.2.4 AZA-MICHAEL ADDITION 1023 34.2.2.5 APPLICATIONS IN TOTAL SYNTHESIS 1025 34.2.3 ACIDIC ACTIVATION 1026 34.2.4 BASIC ACTIVATION 1026 34.2.5 CHALLENGING SUBSTRATES 1027 34.2.5.1 A,(I-DISUBSTITUTED NITROOLEFINS 1027 34.2.5.2 TERMINALLY UNSUBSTITUTED NITROOLEFINS 1030 34.2.5.3 ACETALDEHYDE 1031 34.2.6 MISCELLANEOUS 1031 34.3 ADDITION TO VINYL SULFONES 1032 34.3.1 ENAMINE ACTIVATION OF ALDEHYDES AND KETONES 1032 34.3.2 NON-COVALENT ACTIVATION 1037 34.4 ADDITION TO VINYL SELENONES 1037 CONTENTS I XXI 34.5 SUMMARY AND CONCLUSIONS 1040 ACKNOWLEDGMENTS 1040 REFERENCES 1040 35 ORGANOCATALYZED ASYMMETRIC ARYLATION AND HETEROARYLATION REACTIONS 1043 RENATA MARCIA DE FIGUEIREDO AND JEAN-MARC CAMPAGNE 35.1 INTRODUCTION 1043 35.2 REPRESENTATIVE CLASSES OF ELECTROPHILES 1046 35.2.1 A,P-UNSATURATED ALDEHYDES 1046 35.2.2 A,P-UNSATURATED ENONES 1047 35.2.3 NITROOLEFINS 1048 35.2.4 CARBONYL COMPOUNDS 1049 35.2.5 IMINES (AZA-FRIEDEL-CRAFTS REACTION) 1050 35.2.6 OTHER ELECTROPHILES 1051 35.3 FRIEDEL-CRAFTS IN ORGANOCASCADE TRANSFORMATIONS 1053 35.4 APPLICATION IN BIOLOGICALLY INTERESTING AND NATURAL PRODUCT SYNTHESES 1057 35.5 MISCELLANEOUS 1061 35.6 CONCLUSION 1062 REFERENCES 1063 PART IV RING-FORMING REACTIONS 1067 36 INTRAMOLECULAR REACTIONS 1069 YOU-CAI XIAO AND YING-CHUN CHEN 36.1 INTRODUCTION 3069 36.2 INTRAMOLECULAR RING-FORMING REACTIONS VIA COVALENT CATALYSIS 1070 36.2.1 ENAMINE CATALYSIS 1070 36.2.2 IMINIUM CATALYSIS 1073 36.2.3 SOMO CATALYSIS 1075 36.2.4 CARBENE CATALYSIS 1077 36.2.5 LEWIS BASE CATALYSIS OF TERTIARY AMINES OR PHOSPHINES 1079 36.3 INTRAMOLECULAR RING-FORMING REACTIONS BY NON-COVALENT CATALYSIS 1081 36.3.1 BRANSTED ACID CATALYSIS 1081 36.3.2 BIFUNCTIONAL CATALYSIS 1085 36.4 CONCLUSION 1087 REFERENCES 1087 37 FORMATION OF 3-, 4- AND 5-MEMBERED CYCLES BY INTERMOLECULAR REACTIONS 1091 HILINE PELLISSIER 37.1 INTRODUCTION 1091 37.2 ORGANOCATALYTIC ASYMMETRIC SYNTHESIS OF FIVE-MEMBERED CYCLES 1092 XXII | CONTENTS 37.2.1 SYNTHESIS OF FIVE-MEMBERED CYCLES VIA [3+2] CYDOADDITIONS 1092 37.2.1.1 [3+2] CYDOADDITIONS OF NITRONES 1092 37.2.1.2 [3+2] CYDOADDITIONS OF AZOMETHINE YLIDES 1096 37.2.1.3 MISCELLANEOUS [3+2] CYDOADDITIONS 1098 37.2.2 FIVE-MEMBERED CYCLES VIA DOMINO REACTIONS 1101 37.2.2.1 DOMINO REACTIONS INITIATED BY THE MICHAEL REACTION 1101 37.2.2.2 MISCELLANEOUS DOMINO REACTIONS 1110 37.3 ORGANOCATALYTIC ASYMMETRIC SYNTHESIS OF FOUR-MEMBERED CYCLES 1112 37.4 ORGANOCATALYTIC ASYMMETRIC SYNTHESIS OF THREE-MEMBERED CYCLES 1115 37.4.1 SYNTHESIS OF CYCLOPROPANES 1115 37.4.2 SYNTHESIS OF AZIRIDINES 1120 37.5 CONCLUSION 1123 REFERENCES 1124 38 DIELS-ALDER AND HETERO-DIELS-ALDER REACTIONS 1131 HAIFENG DU AND KUILING DING 38.1 INTRODUCTION 1131 38.2 ORGANOCATALYTIC DIELS-ALDER REACTION 1132 38.2.1 CHIRAL SECONDARY OR PRIMARY AMINES AS CATALYSTS 1132 38.2.1.1 CHIRAL SECONDARY AMINE 1132 38.2.1.2 CHIRAL PRIMARY AMINE 1140 38.2.2 CHIRAL BRANSTED ACIDS CATALYSTS (HYDROGEN-BONDING OR BRANSTED ACID ACTIVATION) 1142 38.2.3 CHIRAL BIFUNCTIONAL CATALYSTS 1144 38.3 ORGANOCATALYSIS OF OXA-HETERO-DIELS-ALDER REACTION 1147 38.3.1 CHIRAL BASES AS CATALYSTS 1148 38.3.2 CHIRAL BRANSTED ACIDS AS CATALYSTS 1150 38.3.3 CHIRAL N-HETEROCYDIC CARBENES AS CATALYSTS 1152 38.4 ORGANOCATALYSIS OF AZA-HETERO-DIELS-ALDER REACTION 1154 38.4.1 CHIRAL CARBENES AS CATALYSTS 1154 38.4.2 CHIRAL AMINES AS CATALYSTS 1155 38.4.3 CHIRAL BRANSTED ACIDS AS CATALYSTS 1157 38.5 CONCLUSION 1159 REFERENCES 1160 PART V INCREASING COMPLEXITY 1163 39 ORGANOCATALYTIC RADICAL AND ELECTRON TRANSFER REACTIONS 1165 THIBAULT CALLAVARDIN AND PETER I. DALKO 39.1 INTRODUCTION 1165 39.2 CHEMICALLY INDUCED OXIDATIVE ELECTRON-TRANSFER REACTIONS 1166 39.2.1 OXAMINATION REACTIONS 1169 39.2.2 ADDITIONS TO OLEFINS AND ALKYNES 1169 CONTENTS XXIII 39.2.3 ASYMMETRIC INTERMOLECULAR ALLYLATION OF ALDEHYDES 1170 39.2.4 ASYMMETRIC ALLYLATION OF KETONES 1172 39.2.5 INTRAMOLECULAR ASYMMETRIC ALLYLATIONS 1172 39.2.6 A-ENOLATION 1173 39.2.7 A-VINYLATION 1174 39.2.8 CARBO-OXIDATION OF STYRENES 1175 39.2.9 POLYENE CYDIZATIONS 1175 39.2.10 INTRAMOLECULAR A-ARYLATION 1176 39.2.11 CASCADE CYDOADDITIONS 1177 39.2.12 ASYMMETRIC NITROALKYLATION OF ALDEHYDES 1180 39.3 PHOTOREDOX CATALYSIS 1180 39.3.1 A-ALKYLATION OF ALDEHYDES 1182 39.3.2 A-BENZYLATION OF ALDEHYDES 1184 39.3.3 A-TRIFLUOROMETHYLATION OF ALDEHYDES 1185 39.4 PHOTOCHEMICAL ASYMMETRIC SYNTHESIS 1186 39.5 CONCLUSION 1188 REFERENCES 1189 40 ORGANOCATALYTIC SIGMATROPIC REACTIONS 1191 CUILLEM VALERO AND ALBERT MOYANO 40.1 INTRODUCTION 1191 40.2 STEGLICH AND RELATED REARRANGEMENTS 1192 40.3 1,3-SIGMATROPIC REARRANGEMENTS 1203 40.4 1,4-SIGMATROPIC REARRANGEMENTS 1207 40.5 2,3-SIGMATROPIC REARRANGEMENTS 1208 40.6 3,3-SIGMATROPIC REARRANGEMENTS 1209 40.7 AZA-PETASIS-FERRIER REARRANGEMENT 1215 40.8 PINACOL AND RELATED REARRANGEMENTS 1216 ACKNOWLEDGMENTS 1220 REFERENCES 1220 41 REGIO- AND POSITION SELECTIVE REACTIONS AND DESYMMETRIZATIONS 1225 ALAN C. SPIVEY AND STELLIOS ARSENIYADIS 41.1 INTRODUCTION 1225 41.2 KINETIC RESOLUTION OF ALCOHOLS 1225 41.2.1 ACYLATION-BASED PROCESSES 1225 41.2.1.1 MECHANISTIC STUDIES 1226 41.2.1.2 SYNTHETIC STUDIES 1229 41.2.2 PHOSPHORYLATION-BASED PROCESS 1251 41.2.3 SULFONYLATION- AND SULFINYLATION-BASED PROCESS 1256 41.2.4 SILYLATION-BASED PROCESS 1258 41.3 KINETIC RESOLUTION OF AMINES 1263 41.3.1 ACYLATION-BASED PROCESS 1263 41.4 CONCLUDING REMARKS 1278 REFERENCES 1279 XXIV | CONTENTS 42 THREE OR MORE COMPONENTS REACTIONS (SINGLE CATALYST SYSTEMS) 1285 RENT TANNERT, ANTONIO MORAN, AND PAOLO MELCHIORRE 42.1 GENERAL INTRODUCTION 1285 42.2 COVALENT MODES OF CATALYSIS-DEVELOPING MCRS BY ASYMMETRIC AMINOCATALYSIS 1287 42.2.1 ASYMMETRIC MCRS BASED ON A SINGLE AMINOCATALYTIC STEP 1288 42.2.2 ASYMMETRIC MCRS BASED ON TWO AMINOCATALYTIC STEPS 1294 42.2.3 ASYMMETRIC MCRS BASED ON THREE OR MORE AMINOCATALYTIC STEPS 1300 42.2.4 ONE-POT ASYMMETRIC MCRS FOR THE PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS 1307 42.3 NON-COVALENT MODES OF CATALYSIS 1309 42.3.1 INTRODUCTION 1309 42.3.2 MANNICH REACTIONS 1310 42.3.3 STRECKER REACTIONS 1314 42.3.4 KABACHNIK-FIELDS REACTION 1314 42.3.5 PETASIS REACTION 1315 42.3.6 UGI-TYPE REACTION 1317 42.3.7 REDUCTIVE ANIMATION 1317 42.3.8 HANTZSCH DIHYDROPYRIDINE AND RELATED REACTIONS 1319 42.3.9 BIGINELLI REACTIONS 1321 42.3.10 1,3-DIPOLAR (HUISGEN) CYCLOADDITION REACTIONS 1322 42.3.11 DIELS-ALDER REACTIONS 1324 42.3.12 OTHER REACTIONS 1325 42.4 MERGING COVALENT AND NON-COVALENT ACTIVATION MODES 1325 42.5 SUMMARY AND OUTLOOK 1326 ACKNOWLEDGMENTS 1327 REFERENCES 1327 43 MULTI-CATALYST SYSTEMS 1333 LIU/EN XU, HUAMENG YANG, AND ZHIHUI SHAO 43.1 INTRODUCTION 1333 43.2 COMBINATIONAL USE OF DUAL BRANSTED ACIDS 1334 43.3 COMBINATIONAL USE OF CHIRAL BRONSTED ACID AND CHIRAL OR ACHIRAL LEWIS BASE 1335 43.4 CARBENE-BASED DUAL ORGANOCATALYSIS 1338 43.5 AMINO CATALYST-BASED COOPERATIVE CATALYSIS WITH MULTIFARIOUS CO-CATALYSTS 1343 43.6 CONCLUSIONS 1354 ACKNOWLEDGMENTS 1355 REFERENCES 1355 CONTENTS | XXV 44 ORGANOCATALYSIS IN TOTAL SYNTHESIS 1359 EUGENIA MARQUIS-LDPEZ AND RAQUEL P. HERRERA 44.1 INTRODUCTION 1359 44.2 AMINOCATALYSIS IN NATURAL PRODUCT SYNTHESIS 1359 44.2.1 ENAMINE CATALYSIS 1360 44.2.2 DIENAMINE CATALYSIS 1363 44.2.3 IMINIUM CATALYSIS 1363 44.2.4 ORGANOCASCADE CATALYSIS: COMBINATIONS OF ENAMINE AND IMINIUM CATALYSIS 1365 44.3 HYDROGEN BOND CATALYSIS IN TOTAL SYNTHESIS 1365 44.3.1 PHOSPHORIC ACIDS 1366 44.3.2 (THIO)UREA ORGANOCATALYZED PROCESSES 1368 44.4 CINCHONA ALKALOIDS IN TOTAL SYNTHESIS 1370 44.5 PHASE-TRANSFER CATALYSIS IN TARGET MOLECULE SYNTHESIS 1371 44.6 INDUSTRIAL APPLICATIONS OF ORGANOCATALYSIS 1373 44.6.1 AMINOCATALYSIS IN THE INDUSTRIAL SECTOR 1373 44.6.2 THIOUREA CATALYSIS AT THE INDUSTRIAL SCALE 1374 44.6.3 CINCHONA ALKALOIDS AT THE INDUSTRIAL LEVEL 1375 44.6.4 PHASE-TRANSFER CATALYSIS IN INDUSTRY 1376 44.7 CONCLUSIONS 1376 REFERENCES 1377 INDEX 1385
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spellingShingle Comprehensive enantioselective organocatalysis catalysts, reactions, and applications
Organokatalyse (DE-588)7636906-7 gnd
Asymmetrische Synthese (DE-588)4135603-2 gnd
subject_GND (DE-588)7636906-7
(DE-588)4135603-2
(DE-588)4143413-4
title Comprehensive enantioselective organocatalysis catalysts, reactions, and applications
title_auth Comprehensive enantioselective organocatalysis catalysts, reactions, and applications
title_exact_search Comprehensive enantioselective organocatalysis catalysts, reactions, and applications
title_full Comprehensive enantioselective organocatalysis catalysts, reactions, and applications ed. by Peter I. Dalko
title_fullStr Comprehensive enantioselective organocatalysis catalysts, reactions, and applications ed. by Peter I. Dalko
title_full_unstemmed Comprehensive enantioselective organocatalysis catalysts, reactions, and applications ed. by Peter I. Dalko
title_short Comprehensive enantioselective organocatalysis
title_sort comprehensive enantioselective organocatalysis catalysts reactions and applications
title_sub catalysts, reactions, and applications
topic Organokatalyse (DE-588)7636906-7 gnd
Asymmetrische Synthese (DE-588)4135603-2 gnd
topic_facet Organokatalyse
Asymmetrische Synthese
Aufsatzsammlung
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