Enantiocontrol in the bakers' yeast reduction of trifluoroacetylbiphenyl derivatives

✍ Scribed by Tamotsu Fujisawa; Seiji Tanaka; Yoshio Onogawa; Makoto Shimizu

• Book ID: 104260850
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 297 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00052-0

✦ Synopsis

The bakers' yeast reduction of trifluoroacetyl derivatives was examined in the presence of various esters of methanethiosulfonate. The yeast reduction of 4-bromo-4'-trifluoroacetylbiphenyl using the cyclohexylmethyl methanethiosulfonate resulted in the R product with the highest enantiomeric excess of 96% ee, which is compared with the reduction without the additive to give the corresponding alcohol with 84% ee. On the other hand, in the case of 4-hyrdoxy-4'-trifluoroacetylbiphenyl, the highest enantioselectivity was observed also using cyclohexylmethyl methanethiosalfonate to give the R-product with 90% ee, in contrast with the reduction without the additives to give the same product with 77% ee.