Synthesis of Chiral Menthoxymethyl Ether of Phenol and Substituted Phenol and their Use in Directed Ortho Metalation

Abstract

Synthesis of chiral acetals of phenol and bromophenol was carried out using (-) menthol as a pure chiral auxiliary. Metalation of these chiral acetals, followed by nucleophilic attack on different aromatic and aliphatic aldehydes produced chiral products through directed ortho metalation (DoM). Chiral menthoxymethyl (OMen) is developed as a new oxygen based chiral directed metalation group (DMG) for benzene and substituted benzene.