Enantiodivergent Synthesis of Tetra-ortho-Substituted Biphenyls by Enzymatic Desymmetrization

Axially chiral, tetra-ortho-substituted biphenyl derivatives were efficiently synthesized through desymmetrization of sigma-symmetric precursors by enzyme-catalyzed hydrolysis. Both of the enantiomers were accessible in highly enantioselective manner and in high yield by suitable choice of enzyme.

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Bibliographic Details
Published inSynlett no. 6; pp. 941 - 944
Main Authors Okuyama, Kumi, Shingubara, Koji, Tsujiyama, Shin-ichiro, Suzuki, Keisuke, Matsumoto, Takashi
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
biphenyl
AXIALLY CHIRAL BIARYLS
asymmetric synthesis
desymmetrization
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
enzyme catalysis
FACILE
hydrolysis
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Summary:Axially chiral, tetra-ortho-substituted biphenyl derivatives were efficiently synthesized through desymmetrization of sigma-symmetric precursors by enzyme-catalyzed hydrolysis. Both of the enantiomers were accessible in highly enantioselective manner and in high yield by suitable choice of enzyme.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0028-1088215