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

Kengo Kasama; Hiroshi Aoyama; Shuji Akai

doi:10.1002/ejoc.201901583

journal article Jan 15, 2020

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

Kengo Kasama Hiroshi Aoyama

Shuji Akai

European Journal of Organic Chemistry Vol. 2020 No. 6 pp. 654-661 · Wiley

View at Publisher Save 10.1002/ejoc.201901583

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.

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Details

Published: Jan 15, 2020
Vol/Issue: 2020(6)
Pages: 654-661
License: View

Authors

K

Kengo Kasama

Graduate School of Pharmaceutical Sciences Osaka University 1‐6, Yamadaoka, Suita 565‐0871 Osaka Japan

H

Hiroshi Aoyama

Graduate School of Pharmaceutical Sciences Osaka University 1‐6, Yamadaoka, Suita 565‐0871 Osaka Japan

S

Shuji Akai

Graduate School of Pharmaceutical Sciences Osaka University 1‐6, Yamadaoka, Suita 565‐0871 Osaka Japan

Funding

Japan Society for the Promotion of Science Award: 18HO4411

Japan Agency for Medical Research and Development Award: JP19am0101084

Cite This Article

Kengo Kasama, Hiroshi Aoyama, Shuji Akai (2020). Enantiodivergent Synthesis of Axially Chiral Biphenyls from σ‐Symmetric 1,1'‐Biphenyl‐2,6‐diol Derivatives by Single Lipase‐Catalyzed Acylative and Hydrolytic Desymmetrization. European Journal of Organic Chemistry, 2020(6), 654-661. https://doi.org/10.1002/ejoc.201901583

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

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