Enantiodivergent Synthesis of Axially Chiral Biphenyls from σ‐Symmetric 1,1'‐Biphenyl‐2,6‐diol Derivatives by Single Lipase‐Catalyzed Acylative and Hydrolytic Desymmetrization

Abstract

The enzymatic acylative desymmetrization of σ‐symmetric 2'‐halo‐1,1'‐biphenyl‐2,6‐diols was achieved for the first time using commercially available Burkholderia cepacia lipase immobilized on diatomaceous earth to give ( S )‐mono esters. The hydrolytic desymmetrization of the corresponding diacetates was also achieved using the same lipase to give ( R )‐mono esters. Our results, therefore, demonstrate that a single lipase can conduct the enantiodivergent synthesis of axially chiral biphenyl compounds in high chemical and optical yields.