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Catalytic Asymmetric Exo-Selective [C+NC+CC] Reaction

Author:
Joseph, Ryan, Murray, Charles, Garner, Philip
Source:
Organic letters 2014 v.16 no.6 pp. 1550-1553
ISSN:
1523-7052
Subject:
acetaldehyde, alkenes, catalysts, chemical reactions, chemical structure, pyrrolidines
Abstract:
A catalytic asymmetric version of the exo-selective [C+NC+CC] reaction is reported. This multicomponent reaction utilizes a readily prepared achiral glycyl sultam as the “NC” component and commercially available catalyst components. The method can be applied to a variety of aldehydes (“C” component) and activated alkenes (“CC” component) to provide substituted pyrrolidines in good yields and high enantioselectivities. Of particular note is the ability to employ labile enolizable aldehydes (e.g., acetaldehyde and propionaldehyde) in this reaction.
Agid:
5788422