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Stereoselective Substitution of Configurationally Labile α‐Bromo Arylacetates with Amines and Azlactones by L ‐Threonine‐Mediated Crystallization‐Induced Dynamic Resolution
Author(s) -
Park SeHee,
Park Yong Sun
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600201
Subject(s) - chemistry , stereoselectivity , crystallization , aryl , amine gas treating , nucleophilic substitution , stereochemistry , resolution (logic) , nucleophilic aromatic substitution , nucleophile , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , alkyl , artificial intelligence , computer science
We developed a highly stereoselective C–N and C–C bond‐forming reaction by carrying out a crystallization‐induced dynamic resolution (CIDR) of α‐bromo arylacetates followed by a stereoselective substitution reaction with an amine or azlactone nucleophile. Applications of this synthetic method to the preparation of highly enantioenriched nitrogen‐containing six‐membered heterocycles and α,β‐disubstituted aspartates are also presented.