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Lipase‐Catalyzed Dynamic Kinetic Resolution of C 1 ‐ and C 2 ‐Symmetric Racemic Axially Chiral 2,2′‐Dihydroxy‐1,1′‐biaryls
Author(s) -
Moustafa Gamal A. I.,
Oki Yasuhiro,
Akai Shuji
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804161
Subject(s) - racemization , kinetic resolution , lipase , enantiomer , axial symmetry , chemistry , catalysis , kinetic energy , enantiomeric excess , enantioselective synthesis , chromophore , resolution (logic) , axial chirality , stereochemistry , combinatorial chemistry , computational chemistry , organic chemistry , enzyme , physics , quantum mechanics , artificial intelligence , computer science
Abstract We have discovered that the racemization of configurationally stable, axially chiral 2,2′‐dihydroxy‐1,1′‐biaryls proceeds with a catalytic amount of a cyclopentadienylruthenium(II) complex at 35–50 °C. Combining this racemization procedure with lipase‐catalyzed kinetic resolution led to the first lipase/metal‐integrated dynamic kinetic resolution of racemic axially chiral biaryl compounds. The method was applied to the synthesis of various enantio‐enriched C 1 ‐ and C 2 ‐symmetric biaryl diols in yields of up to 98 % and enantiomeric excesses of up to 98 %, which paves the way for new developments in the field of asymmetric synthesis.