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Enantioselective anti-Mannich reaction catalyzed by modularly designed organocatalysts

Author:
Konda, Swapna, Zhao, John C.-G.
Source:
Tetrahedron 2018 v.74 no.42 pp. 6166-6172
ISSN:
0040-4020
Subject:
Cinchona, aldehydes, alkaloids, carboxylic acids, chemical reactions, chemical structure, diastereoselectivity, enantioselectivity, ketones
Abstract:
A highly stereoselective method for achieving the anti-Mannich reaction of aldehydes and ketones with ethyl (4-methoxyphenylimino)acetate was realized using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and (R)-pyrrolidien-3-carboxylic acid in the reaction media. The desired anti-Mannich products were obtained in good to excellent yields (up to 93%), excellent diastereoselectivities (up to 99:1 dr), and good to high enantioselectivities (up to 99% ee).
Agid:
6130909