Stereoselective Substitution of Configurationally Labile α-Bromo Arylacetates with Amines and Azlactones by L -Threonine-Mediated Crystallization-Induced Dynamic Resolution

Article abstract of DOI:10.1002/ejoc.201600201

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.