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Phosphine‐Catalyzed Asymmetric Umpolung Addition of Trifluoromethyl Ketimines to Morita–Baylis–Hillman Carbonates
Author(s) -
Chen Peng,
Yue Zhenting,
Zhang Junyou,
Lv Xi,
Wang Lei,
Zhang Junliang
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201607918
Subject(s) - umpolung , stereocenter , trifluoromethyl , enantioselective synthesis , chemistry , phosphine , organocatalysis , catalysis , baylis–hillman reaction , organic chemistry , substrate (aquarium) , combinatorial chemistry , alkyl , nucleophile , oceanography , geology
A novel phosphine‐catalyzed, highly enantioselective umpolung addition of trifluoromethyl ketimines to Morita–Baylis–Hillman carbonates was developed and it provides facile access to optically active trifluoromethyl amines with a chiral tertiary stereocenter under mild reaction conditions. The salient features of this reaction include general substrate scope, mild reaction conditions, good yields, high enantioselectivity, ease of scale‐up to gram scale, and further transformations of the products.