Lipase-catalyzed dynamic kinetic resolution of C 1 - and C 2 -symmetric racemic axially chiral 2,2′-dihydroxy-1,1′-biaryls

Moustafa, Gamal A. I., Oki, Yasuhiro and Akai, Shuji (2018) Lipase-catalyzed dynamic kinetic resolution of C 1 - and C 2 -symmetric racemic axially chiral 2,2′-dihydroxy-1,1′-biaryls. Angewandte Chemie International Edition, 57 (32), 10278-10282. (doi:10.1002/anie.201804161).

Record type: Article

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 C1‐ and C2‐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.

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