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Catalytic Asymmetric Mannich‐Type Reaction of N ‐Alkylidene‐α‐Aminoacetonitrile with Ketimines
Author(s) -
Lin Shaoquan,
Kawato Yuji,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2015
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.201412377
Subject(s) - stereocenter , chemistry , catalysis , vicinal , lewis acids and bases , stereoselectivity , enantioselective synthesis , combinatorial chemistry , brønsted–lowry acid–base theory , organic chemistry , aldol reaction , organocatalysis
Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Brønsted base cooperative catalyst allows for an efficient stereoselective coupling of N ‐alkylidene‐α‐aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra‐ and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading.