N-Benzoyl-L-Threonine-Isopropyl-Ester-Mediated Crystallization-Induced Dynamic Resolution of α-Bromo Arylacetates for the Asymmetric Synthesis of α-Thio and α-Oxy Arylacetates

N-Benzoyl-L-threonine-isopropyl-ester-mediated crystallization-induced dynamic resolution (CIDR) of configurationally labile α-bromo arylacetates has been investigated. The CIDR was successfully used for the asymmetric preparation of these compounds with up to 98:2 dr, under solution and solvent-free conditions. Subsequent nucleophilic substitution reactions with sulfur and oxygen nulceophiles gave α-thio and α-oxy arylacetates with up to 98:2 dr. The method was further developed for the preparation of highly enantioenriched 2-phenylthio-2-arylethanols with up to 97:3 er, and 1,4-benzoxazin-3-ones with up to 94:6 er.