A four-component reaction involving in situ generated organometallic reagents: straightforward access to β-amino esters.

Chemistry. 2013  22;19(17):5238-41.

Le Gall E, Léonel E.

Electrochimie et Synthèse Organique, Institut de Chimie et des Matériaux Paris-Est, UMR 7182 CNRS-Université Paris-Est Créteil Val de Marne, 2-8 rue Henri Dunant, 94320 Thiais, France. [email protected]

 

Abstract

 

Four in one: A straightforward synthesis of β(2,3)-amino esters is described through a new zinc-mediated, cobalt-catalyzed four-component reaction between organic bromides, alkyl acrylates, amines, and aldehydes (see scheme). Synthesis involves a Mannich-related conjugate addition/aza-aldol domino sequence, allowing the formation of three single bonds in one step. A reaction mechanism, emphasizing the crucial role of zinc salts, is described.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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