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Enantioselective Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Silyl Ketene Imines with Isatin‐Derived Ketimines
Author(s) -
Zhao Jiannan,
Fang Bing,
Luo Weiwei,
Hao Xiaoyu,
Liu Xiaohua,
Lin Lili,
Feng Xiaoming
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408730
Subject(s) - ketene , enantioselective synthesis , stereocenter , vicinal , chemistry , isatin , mannich reaction , silylation , yield (engineering) , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , materials science , metallurgy
A highly enantioselective Mannich reaction of silyl ketene imines with isatin‐derived ketimines has been realized by using a chiral N , N′ ‐dioxide/Zn II catalyst. A variety of β‐amino nitriles containing congested vicinal tetrasubstituted stereocenters were obtained with excellent outcomes (up to 98 % yield, >19:1 d.r. and 99 % ee ). Based on the experimental investigations, a possible transition state has been proposed to explain the origin of the asymmetric induction.