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Type: Artigo
Title: Intermolecular Stetter Reactions On Morita-baylis-hillman Adducts: An Approach To Highly Functionalized 1,4-dicarbonyl Compounds
Author: Gomes
Ralph C.; Barcelos
Rosimeire C.; Rodrigues
Manoel T.
Jr.; Santos
Hugo; Coelho
Abstract: We reported herein an N-heterocyclic carbene (NHC)-mediated intermolecular Stetter reaction between oxidized Morita-Baylis-Hillman (MBH) adducts and a variety of aldehydes. This protocol allows the synthesis of highly functionalized 1,4-dicarbonyl compounds. The reaction is an alternative approach to these compounds using commercially available starting materials. This metal-free process exhibits a wide substrate scope, excellent atom economy, compatibility with functionalized substrates and mild reaction conditions. The 1,4-dicarbonyl compounds were prepared in two steps via MBH reactions with overall yields up to 99%. This protocol is easily scalable. The synthetic usefulness of this method was demonstrated in a high yield synthesis of a tri-substituted pyrrole used as an advanced intermediate in the total synthesis of kinase inhibitors as well as in the synthesis of another heterocycles.
Subject: 1,4-dicarbonyl Compounds
Mbh Adducts
Stetter Reaction
Editor: Wiley-V C H Verlag GMBH
Citation: Chemistryselect. Wiley-v C H Verlag Gmbh, v. 2, p. 926 - 930, 2017.
Rights: fechado
Identifier DOI: 10.1002/slct.201602059
Date Issue: 2017
Appears in Collections:Unicamp - Artigos e Outros Documentos

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