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The First Catalytic, Enantioselective Aza‐Henry Reaction of an Unactivated Cyclic Imine
Author(s) -
Amarasinghe Nilupa R.,
Turner Peter,
Todd Matthew H.
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200558
Subject(s) - imine , chemistry , nitromethane , enantiopure drug , enantioselective synthesis , nitroaldol reaction , catalysis , vicinal , acylation , diamine , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry
The aza‐Henry reaction is an efficient route to important chiral, vicinal diamines. Reports of the asymmetric version typically use electron‐deficient acyclic imines. We report the first example of a catalytic, asymmetric aza‐Henry reaction on an unfunctionalized cyclic imine that gives access to enantiopure diamine derivatives under experimentally straightforward conditions. The stereocentre is established through the initial nitromethane addition to the imine. The scalemic intermediate may be trapped through acylation, then crystallized.