Enantioselective synthesis of 2,3-diphenyl-1,4-butanediol via oxidative coupling of phenylacetic acid chiral 1,1'-bi-2-naphthyl ester using TiCl < inf > 4 < /inf > /Et < inf > 3 < /inf > N

Abstract

Oxidative coupling of phenylacetic acid ester of homochiral 1,1'-bi-2-naphthol 2 was achieved by reaction with TiCl4/Et3N to obtain the corresponding 2,3-diphenylsuccinic acid derivative 3, which on reduction using the NaBH4/I2 reagent gives homochiral 2,3-diphenyl-1,4-butanediol. X-Ray structural analysis was carried out for the compounds (R)-(+)-2 and (R,R,R)-(-)-3. Copyright (C) 2000.