Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride

Article abstract of DOI:10.1016/0040-4039(96)00964-1

The first enantioselective synthesis of cetirizine hydrochloride (1) has been developed using the highly stereospecific chiral oxazaborolidine (CBS) reduction of 4-[η⁶-chromium tricarbonylbenzoyl]chlorobenzene to establish the benzhydryl stereocenter. The chromium tricarbonyl unit also served as stereocontroller to allow the stereospecific displacement of hydroxyl by amino at the benzylic stereocenter, as outlined in Scheme 1.