NOVEL PROTOCOL FOR THE ASYMMETRIC SYNTHESIS OF 3-HYDROXY-2-(4-METHOXYPHENYL)-2,3-DIHYDRO-1,5-BENZOTHIAZEPIN-4(5H)-ONE VIA BAKERS' YEAST REDUCTION

摘要

A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported.Darzens condensation reactions of anisaldehyde with dichloroacetates,followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates.Further reduction of a nitro group and cyclization gave the title compound.