Michael Addition Initiated Carbocyclization Sequences with Nitroolefins for the Stereoselective Synthesis of Functionalized Heterocyclic and Carbocyclic Systems
The synthesis of various heterocycles and carbocycles (tetrahydrofurans, pyrrolidines, cyclopentanes) has been achieved by using new and efficient ionic addition/cyclization sequences. Nitroolefins play an important role in the Michael addition induced ring‐closing reactions (MIRC) reported in the p...
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| Veröffentlicht in: | Chemistry : a European journal 2009-11, Vol.15 (45), p.12470-12488 |
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| container_title | Chemistry : a European journal |
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| creator | Dumez, Estelle Durand, Anne-Catherine Guillaume, Martial Roger, Pierre-Yves Faure, Robert Pons, Jean-Marc Herbette, Gaëtan Dulcère, Jean-Pierre Bonne, Damien Rodriguez, Jean |
| description | The synthesis of various heterocycles and carbocycles (tetrahydrofurans, pyrrolidines, cyclopentanes) has been achieved by using new and efficient ionic addition/cyclization sequences. Nitroolefins play an important role in the Michael addition induced ring‐closing reactions (MIRC) reported in the present article, with various substituted alcohols, amines, Grignard reactants, or malonate derivatives acting as the nucleophile partner. The optimized cascade reactions were high yielding in most cases and highly stereoselective, creating up to three stereogenic centers starting from achiral substrates.
Complexity from simplicity: New Michael addition initiated ionic carbocyclization sequences have been developed that allow stereoselective syntheses of a variety of highly functionalized carbo‐ and heterocyclic compounds starting from simple achiral nitroolefins and a variety of nucleophiles (alcohols, amines, malonates, Grignard reagents), with the concomitant creation of three stereogenic centers (see scheme). |
| doi_str_mv | 10.1002/chem.200901433 |
| format | Article |
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Complexity from simplicity: New Michael addition initiated ionic carbocyclization sequences have been developed that allow stereoselective syntheses of a variety of highly functionalized carbo‐ and heterocyclic compounds starting from simple achiral nitroolefins and a variety of nucleophiles (alcohols, amines, malonates, Grignard reagents), with the concomitant creation of three stereogenic centers (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.200901433</identifier><identifier>PMID: 19834936</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkenes - chemistry ; Chemical Sciences ; Cyclization ; cycloaddition ; Cyclopentanes - chemical synthesis ; Cyclopentanes - chemistry ; Cyclopropanes - chemical synthesis ; Cyclopropanes - chemistry ; domino reactions ; Furans - chemical synthesis ; Furans - chemistry ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Michael addition ; Molecular Structure ; nitroolefins ; Organic chemistry ; Stereoisomerism</subject><ispartof>Chemistry : a European journal, 2009-11, Vol.15 (45), p.12470-12488</ispartof><rights>Copyright © 2009 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4163-4a21f934e5ce8182d2a1b76f8cf36ecfd639abe6cedc26eb5352f490b1f843d83</citedby><cites>FETCH-LOGICAL-c4163-4a21f934e5ce8182d2a1b76f8cf36ecfd639abe6cedc26eb5352f490b1f843d83</cites><orcidid>0000-0002-3374-2508 ; 0000-0003-4479-4626 ; 0000-0003-4916-3006</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.200901433$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.200901433$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19834936$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00677491$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Dumez, Estelle</creatorcontrib><creatorcontrib>Durand, Anne-Catherine</creatorcontrib><creatorcontrib>Guillaume, Martial</creatorcontrib><creatorcontrib>Roger, Pierre-Yves</creatorcontrib><creatorcontrib>Faure, Robert</creatorcontrib><creatorcontrib>Pons, Jean-Marc</creatorcontrib><creatorcontrib>Herbette, Gaëtan</creatorcontrib><creatorcontrib>Dulcère, Jean-Pierre</creatorcontrib><creatorcontrib>Bonne, Damien</creatorcontrib><creatorcontrib>Rodriguez, Jean</creatorcontrib><title>Michael Addition Initiated Carbocyclization Sequences with Nitroolefins for the Stereoselective Synthesis of Functionalized Heterocyclic and Carbocyclic Systems</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>The synthesis of various heterocycles and carbocycles (tetrahydrofurans, pyrrolidines, cyclopentanes) has been achieved by using new and efficient ionic addition/cyclization sequences. Nitroolefins play an important role in the Michael addition induced ring‐closing reactions (MIRC) reported in the present article, with various substituted alcohols, amines, Grignard reactants, or malonate derivatives acting as the nucleophile partner. The optimized cascade reactions were high yielding in most cases and highly stereoselective, creating up to three stereogenic centers starting from achiral substrates.
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Nitroolefins play an important role in the Michael addition induced ring‐closing reactions (MIRC) reported in the present article, with various substituted alcohols, amines, Grignard reactants, or malonate derivatives acting as the nucleophile partner. The optimized cascade reactions were high yielding in most cases and highly stereoselective, creating up to three stereogenic centers starting from achiral substrates.
Complexity from simplicity: New Michael addition initiated ionic carbocyclization sequences have been developed that allow stereoselective syntheses of a variety of highly functionalized carbo‐ and heterocyclic compounds starting from simple achiral nitroolefins and a variety of nucleophiles (alcohols, amines, malonates, Grignard reagents), with the concomitant creation of three stereogenic centers (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>19834936</pmid><doi>10.1002/chem.200901433</doi><tpages>19</tpages><orcidid>https://orcid.org/0000-0002-3374-2508</orcidid><orcidid>https://orcid.org/0000-0003-4479-4626</orcidid><orcidid>https://orcid.org/0000-0003-4916-3006</orcidid></addata></record> |
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| ispartof | Chemistry : a European journal, 2009-11, Vol.15 (45), p.12470-12488 |
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| source | MEDLINE; Access via Wiley Online Library |
| subjects | Alkenes - chemistry Chemical Sciences Cyclization cycloaddition Cyclopentanes - chemical synthesis Cyclopentanes - chemistry Cyclopropanes - chemical synthesis Cyclopropanes - chemistry domino reactions Furans - chemical synthesis Furans - chemistry Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Michael addition Molecular Structure nitroolefins Organic chemistry Stereoisomerism |
| title | Michael Addition Initiated Carbocyclization Sequences with Nitroolefins for the Stereoselective Synthesis of Functionalized Heterocyclic and Carbocyclic Systems |
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