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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Review Article

Organocatalyzed Transient Dienamine-Mediated Diels-Alder Reactions between α,β-Unsaturated Ketones and Alkenes

Author(s): Iosune Arrastia, Ana Arrieta and Fernando P. Cossio*

Volume 15, Issue 5, 2018

Page: [394 - 403] Pages: 10

DOI: 10.2174/1570178615666180102144530

Price: $65

Abstract

Organocatalyzed (4+2) cycloadditions (Diels-Alder reactions) are reviewed in this manuscript. Among the different catalytic alternatives, reactions involving α,β-unsaturated ketones and alkenes are considered. In these processes, substituted cyclohexanones are obtained via HOMO activation generated by amine organocatalysis that generate transient dienamine species. Both concerted and stepwise mechanisms are described. In most cases, excellent regio-, diastereo- and enantiocontrol have been observed.

Keywords: Organocatalysis, diels-Alder reactions, cycloadditions, michael additions, pericyclic reactions, stepwise mechanisms.

Graphical Abstract


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