Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/54342
Type: Artigo de periódico
Title: An asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines
Author: Luna-Freire, KR
Scaramal, JPS
Resende, JALC
Tormena, CF
Oliveira, FL
Aparicio, R
Coelho, F
Abstract: We describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.
Subject: Morita-Baylis-Hillman
Heterocycles
Pyrrolizidines
Heck reaction
Stereoselectivity
Absolute configuration
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/j.tet.2013.10.050
Date Issue: 2014
Appears in Collections:Unicamp - Artigos e Outros Documentos

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