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Enantiodivergent Synthesis of Axially Chiral Biphenyls from σ‐Symmetric 1,1'‐Biphenyl‐2,6‐diol Derivatives by Single Lipase‐Catalyzed Acylative and Hydrolytic Desymmetrization
Author(s) -
Kasama Kengo,
Aoyama Hiroshi,
Akai Shuji
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901583
Subject(s) - desymmetrization , chemistry , lipase , biphenyl , hydrolysis , burkholderia , organic chemistry , diol , catalysis , enantioselective synthesis , stereochemistry , enzyme , bacteria , genetics , biology
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.