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Asymmetric Synthesis of β‐Amino Nitriles through a Sc III ‐Catalyzed Three‐Component Mannich Reaction of Silyl Ketene Imines
Author(s) -
Zhao Jiannan,
Liu Xiaohua,
Luo Weiwei,
Xie Mingsheng,
Lin Lili,
Feng Xiaoming
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201209093
Subject(s) - stereocenter , ketene , chemistry , catalysis , scandium , silylation , mannich reaction , medicinal chemistry , carbon fibers , quaternary carbon , organic chemistry , enantioselective synthesis , materials science , composite number , composite material
A range of β‐amino nitriles containing contiguous tertiary and quaternary stereogenic carbon centers were synthesized by using the title reaction. The reaction was catalyzed by a chiral N , N ′‐dioxide scandium(III) complex under mild reaction conditions. Based on experimental investigations, a possible transition state has been proposed to explain the origin of asymmetric inductivity.