Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/54342
Type: Artigo
Title: An asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines
Author: Luna-Freire, Kristerson R.
Scaramal, João Paulo S.
Resende, Jackson A.L.C.
Tormena, Cláudio F.
Oliveira, Fábio L.
Aparicio, Ricardo
Coelho, Fernando
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.
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-aldeh
Subject: Morita-Baylis-Hillman
Heterociclicos
Pirrolizidina
Reação de Heck
Configuração absoluta
Country: Reino Unido
Editor: Elsevier
Citation: Tetrahedron. Pergamon-elsevier Science Ltd, v. 70, n. 20, n. 3319, n. 3326, 2014.
Rights: fechado
Identifier DOI: 10.1016/j.tet.2013.10.050
Address: https://www.sciencedirect.com/science/article/pii/S0040402013015950
Date Issue: 2014
Appears in Collections:IQ - Artigos e Outros Documentos

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