Dynamic kinetic resolution of (S)-mandelate-derived á-bromo esters in nucleophilic substitution and asymmetric syntheses of 3-substituted morpholin-2-ones

Abstract

Dynamic kinetic resolution of (S)-mandelate-derived α-bromo esters in nucleophilic substitution reaction has been investigated. Substitutions with various alkyl amine nucleophiles in the presence of TBAI and DIEA can provide various α-amino esters up to 81% yield and 97:3 dr. Also, the substitution of α-bromo esters with N-substituted 2-aminoethanol nucleophiles and following spontaneous cyclization provides a practical protocol for asymmetric syntheses of 3-substituted morpholin-2-ones up to 95:5 er. © ARKAT USA, Inc.