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Diastereo- and Enantioselective Three-Component Coupling Approach to Highly Substituted Pyrrolidines

Author:
Chaulagain, Mani Raj, Felten, Albert E., Gilbert, Kevin, Aron, Zachary D.
Source:
Journal of organic chemistry 2013 v.78 no.18 pp. 9471-9476
ISSN:
1520-6904
Subject:
Lewis acids, aldehydes, alkenes, amino acids, catalysts, diamines, enantioselective synthesis, enantioselectivity, models, organic chemistry, pyrrolidines
Abstract:
The enantioselective synthesis of substituted pyrrolidines through a mild Lewis-acid catalyzed three-component coupling reaction between picolinaldehyde, amino acids, and activated olefins is reported. The reaction uses low catalyst loadings of commercially available chiral diamines and copper triflate proposed to self-assemble in conjunction with the chelating aldehydes, 4-substituted-2-picolinaldehydes or 4-methylthiazole-2-carboxaldehyde, to generate a catalyst complex. A model is provided to explain how this complex directs enantioselectivity. This work represents a significant advance in the ease, scope, and cost of producing highly substituted, enantioenriched pyrrolidines.
Agid:
5500391