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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Intermolecular Stetter Reactions on Morita-Baylis-Hillman Adducts: an Approach to Highly Functionalized 1,4-Dicarbonyl Compounds

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Gomes, Ralph C. ; Barcelos, Rosimeire C. ; Rodrigues, Jr., Manoel T. ; Santos, Hugo ; Coelho, Fernando
Total Authors: 5
Document type: Journal article
Source: CHEMISTRYSELECT; v. 2, n. 3, p. 926-930, JAN 2017.
Web of Science Citations: 1

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. (AU)

FAPESP's process: 15/09205-0 - New frontiers of the Morita-Baylis-Hillman reaction: 1) New applications of a bifunctional catalyst derived from imidazole. 2) Studies on the asymmetric synthesis of a natural high-potency sweetener
Grantee:Hugo dos Santos
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
FAPESP's process: 13/10449-5 - Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of molecules of biological interest
Grantee:Fernando Antonio Santos Coelho
Support Opportunities: Regular Research Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC