Abstract
The catalytic enantioselective aza-Michael reaction is an important transformation in organic chemistry, which has been used for the synthesis of a significant amount of nitrogen-containing products for many research areas in chemistry. In this review, we summarize the literature dealing with catalytic enantioselective versions of this transformation, where a small chiral organic molecule which does not contain metal atoms within its structure (the organocatalyst) is employed for promoting the reaction and also for controlling its stereochemical outcome. Several examples highlighting the successful application of this methodology will also be presented, emphasized by the description of the enantioselective total synthesis of several natural products and therapeutics.
Keywords: Organocatalysis, asymmetric synthesis, aza-Michael reaction, conjugate addition, base-catalyzed reaction, pro-nucleophile, carbon-based nucleophilic species, organocatalysts, LUMO, proline-based derivatives, MacMillan-type, stereocontrol, Michael acceptor, stereocenter, chemoselectivity
Current Organic Chemistry
Title: Organocatalytic Enantioselective aza-Michael Reactions
Volume: 16 Issue: 4
Author(s): Efraim Reyes, Maitane Fernandez, Uxue Uria, Jose L. Vicario, Dolores Badia and Luisa Carrillo
Affiliation:
Keywords: Organocatalysis, asymmetric synthesis, aza-Michael reaction, conjugate addition, base-catalyzed reaction, pro-nucleophile, carbon-based nucleophilic species, organocatalysts, LUMO, proline-based derivatives, MacMillan-type, stereocontrol, Michael acceptor, stereocenter, chemoselectivity
Abstract: The catalytic enantioselective aza-Michael reaction is an important transformation in organic chemistry, which has been used for the synthesis of a significant amount of nitrogen-containing products for many research areas in chemistry. In this review, we summarize the literature dealing with catalytic enantioselective versions of this transformation, where a small chiral organic molecule which does not contain metal atoms within its structure (the organocatalyst) is employed for promoting the reaction and also for controlling its stereochemical outcome. Several examples highlighting the successful application of this methodology will also be presented, emphasized by the description of the enantioselective total synthesis of several natural products and therapeutics.
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Cite this article as:
Reyes Efraim, Fernandez Maitane, Uria Uxue, L. Vicario Jose, Badia Dolores and Carrillo Luisa, Organocatalytic Enantioselective aza-Michael Reactions, Current Organic Chemistry 2012; 16 (4) . https://dx.doi.org/10.2174/138527212799499804
DOI https://dx.doi.org/10.2174/138527212799499804 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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