Aminomethylation of Michael Acceptors: Complementary Radical and Polar Approaches Mediated by Dialkylzincs
Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc‐mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin‐trapping experiments and rati...
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| Veröffentlicht in: | Chemistry : a European journal 2012-03, Vol.18 (11), p.3241-3247 |
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| container_title | Chemistry : a European journal |
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| creator | Maury, Julien Mouysset, Dominique Feray, Laurence Marque, Sylvain R. A. Siri, Didier Bertrand, Michèle P. |
| description | Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc‐mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin‐trapping experiments and rationalized by theoretical calculations. Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds.
Radical attack: Phtalimidomethyl iodide and diiodomaleimidomethyl iodide were used as radical precursors in the dialkylzinc‐mediated radical addition to diethyl fumarate (see scheme). The reactions led stereoselectively to functionalized pyrrolizidines. Radical additions and carbozincation followed by transmetalation with copper(I) were shown to be complementary methods to achieve the formal aminomethylation of Michael acceptors. |
| doi_str_mv | 10.1002/chem.201102366 |
| format | Article |
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Radical attack: Phtalimidomethyl iodide and diiodomaleimidomethyl iodide were used as radical precursors in the dialkylzinc‐mediated radical addition to diethyl fumarate (see scheme). The reactions led stereoselectively to functionalized pyrrolizidines. Radical additions and carbozincation followed by transmetalation with copper(I) were shown to be complementary methods to achieve the formal aminomethylation of Michael acceptors.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201102366</identifier><identifier>PMID: 22328494</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activated ; aminomethylation ; Chemical Sciences ; Chemistry ; dialkylzincs ; ESR experiments ; Iodides ; Mathematical analysis ; Organic chemistry ; Precursors ; radical reactions ; Radicals ; theoretical calculations ; Unsaturated ; zinc</subject><ispartof>Chemistry : a European journal, 2012-03, Vol.18 (11), p.3241-3247</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2012 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-c5436-c8400da813e0db1ed2744fd34ea55dc30f4872acbe0308bc40ccc85ae9be5d453</citedby><cites>FETCH-LOGICAL-c5436-c8400da813e0db1ed2744fd34ea55dc30f4872acbe0308bc40ccc85ae9be5d453</cites><orcidid>0000-0003-1561-7233</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,1411,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22328494$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://amu.hal.science/hal-01411153$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Maury, Julien</creatorcontrib><creatorcontrib>Mouysset, Dominique</creatorcontrib><creatorcontrib>Feray, Laurence</creatorcontrib><creatorcontrib>Marque, Sylvain R. A.</creatorcontrib><creatorcontrib>Siri, Didier</creatorcontrib><creatorcontrib>Bertrand, Michèle P.</creatorcontrib><title>Aminomethylation of Michael Acceptors: Complementary Radical and Polar Approaches Mediated by Dialkylzincs</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc‐mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin‐trapping experiments and rationalized by theoretical calculations. Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds.
Radical attack: Phtalimidomethyl iodide and diiodomaleimidomethyl iodide were used as radical precursors in the dialkylzinc‐mediated radical addition to diethyl fumarate (see scheme). The reactions led stereoselectively to functionalized pyrrolizidines. Radical additions and carbozincation followed by transmetalation with copper(I) were shown to be complementary methods to achieve the formal aminomethylation of Michael acceptors.</description><subject>Activated</subject><subject>aminomethylation</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>dialkylzincs</subject><subject>ESR experiments</subject><subject>Iodides</subject><subject>Mathematical analysis</subject><subject>Organic chemistry</subject><subject>Precursors</subject><subject>radical reactions</subject><subject>Radicals</subject><subject>theoretical calculations</subject><subject>Unsaturated</subject><subject>zinc</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkU2P0zAURSMEYsrAliWyxAJYpDzHH0nYVWWYIrUDQgNdWo79qrrjxCVOZyi_HlcdKsQCVpasc6_O082y5xTGFKB4a9bYjgugFAom5YNsREVBc1ZK8TAbQc3LXApWn2VPYtwAQC0Ze5ydFQUrKl7zUbaZtK4LLQ7rvdeDCx0JK7JwZq3Rk4kxuB1CH9-RaWi3HlvsBt3vyRdtndGe6M6Sz8Hrnky22z7oZBPJAq3TA1rS7Ml7p_3N3v90nYlPs0cr7SM-u3_Ps68fLq6ns3z-6fLjdDLPjeBM5qbiAFZXlCHYhqItSs5XlnHUQljDYMWrstCmQWBQNYaDMaYSGusGheWCnWdvjr1r7dW2d20yVkE7NZvM1eEPKKeUCnZLE_vqyCb77zuMg2pdNOi97jDsoqoLKUCWjCXy9T9JWgHwqpY1T-jLv9BN2PVdulnRUkpJK1pAosZHyvQhxh5XJ1cK6rCtOmyrTtumwIv72l3Toj3hv8dMQH0E7pzH_X_q1HR2sfizPD9mXRzwxymr-xuVzi-FWl5dqiVL7lfLa_WN_QLC777O</recordid><startdate>20120312</startdate><enddate>20120312</enddate><creator>Maury, Julien</creator><creator>Mouysset, Dominique</creator><creator>Feray, Laurence</creator><creator>Marque, Sylvain R. A.</creator><creator>Siri, Didier</creator><creator>Bertrand, Michèle P.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-1561-7233</orcidid></search><sort><creationdate>20120312</creationdate><title>Aminomethylation of Michael Acceptors: Complementary Radical and Polar Approaches Mediated by Dialkylzincs</title><author>Maury, Julien ; Mouysset, Dominique ; Feray, Laurence ; Marque, Sylvain R. 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Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds.
Radical attack: Phtalimidomethyl iodide and diiodomaleimidomethyl iodide were used as radical precursors in the dialkylzinc‐mediated radical addition to diethyl fumarate (see scheme). The reactions led stereoselectively to functionalized pyrrolizidines. Radical additions and carbozincation followed by transmetalation with copper(I) were shown to be complementary methods to achieve the formal aminomethylation of Michael acceptors.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>22328494</pmid><doi>10.1002/chem.201102366</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-1561-7233</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Activated aminomethylation Chemical Sciences Chemistry dialkylzincs ESR experiments Iodides Mathematical analysis Organic chemistry Precursors radical reactions Radicals theoretical calculations Unsaturated zinc |
| title | Aminomethylation of Michael Acceptors: Complementary Radical and Polar Approaches Mediated by Dialkylzincs |
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