New reduction reaction of benzylic alcohols with acid and proof of the intermolecular hydride shift mechanism

Article abstract of DOI:10.3987/COM-99-8786

The new reduction reaction of the hydroxy groups of 4-hydroxy-4-phenyl- 1,2,3,4-tetrahydroisoquinolines (1) to the corresponding alkanes (2) with mineral and Lewis acids is reported. A stereoselective intermolecular hydride shift mechanism of the reduction was proved by reaction of the deuterated derivatives (14 and 15) of 1a with 10N HCl-C₂H₅OH and BBr3 in CH₃CN.