A Facile, Versatile, and Mild Morita-Baylis-Hillman-Type Reaction for the Modular One-Pot Synthesis of Highly Functionalized MBH Adducts
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
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| Data(s) |
11/09/2013
11/09/2013
2012
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| Resumo |
MoritaBaylisHillman derivatives have been extensively investigated as intermediates in the preparation of important classes of compounds. However, there are intrinsic limitations regarding the structure of the Michael electrophile acceptors, the aldehydes, and the catalysts. Therefore, this transformation has several drawbacks, including, for example, its long reaction times. Herein we present a simple, general, fast, and high-yielding protocol for the one-pot synthesis of MoritaBaylisHillman derivatives. Our approach is driven by a lithium selenolate Michael/aldol operation with concomitant O-functionalization/selenoxide elimination cascade sequences. Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) Conselho Nacional de Pesquisa e Desenvolvimento (CNPq) Conselho Nacional de Pesquisa e Desenvolvimento (CNPq) Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) |
| Identificador |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WEINHEIM, v. 752, n. 18, pp. 3431-3436, JUN, 2012 1434-193X http://www.producao.usp.br/handle/BDPI/33253 10.1002/ejoc.201200371 |
| Idioma(s) |
eng |
| Publicador |
Wiley-V C H Verlag GmbH WEINHEIM |
| Relação |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
| Direitos |
closedAccess Copyright WILEY-V C H VERLAG GMBH |
| Palavras-Chave | #MULTICOMPONENT REACTIONS #DOMINO REACTIONS #MICHAEL ADDITION #ALDOL REACTIONS #SELENIUM #ALLYLIC SUBSTITUTION #ACETATES #ALKYLATION #BUTENOLIDES #CARBONATES #ALDEHYDES #INDOLES #CHEMISTRY, ORGANIC |
| Tipo |
article original article publishedVersion |
