Enzymatic Resolution and Decarboxylative Functionalization of α‐Sulfinyl Esters

Abstract

Abstractα‐Sulfinyl esters can be readily prepared through thiol substitution of α‐bromo esters followed by oxidation to the sulfoxide. Enzymatic resolution with lipoprotein lipase provides both the unreacted esters and corresponding α‐sulfinyl carboxylic acids in high yields and enantiomeric ratios. Subsequent decarboxylative halogenation, dihalogenation, trihalogenation and cross‐coupling gives rise to functionalized sulfoxides. The method has been applied to the asymmetric synthesis of a potent inhibitor of 15‐prostaglandin dehydrogenase.