Lewis based-catalyzed acylative KRs of biaryl diol derivatives

February 23, 2024

• Title:       

  Lewis based-catalyzed acylative KRs of biaryl diol derivatives

• Image Source:

  Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols

• Mark:

  Scheme 1

• Associated context:

  Small molecule Lewis base catalyzed acylative KRs of these  substrates has not been widely explored. Sibi has reported the acylative KR of mono-protected biaryl diols using  afluxionally chiral DMAP catalyst with moderate to good  selectivity factors (Scheme 1a, s = 10–50), however the KR of unprotected chiral biaryl diols remains surprisingly  underdeveloped. To the best of our knowledge, only one such  method has been reported by Zhao by utilizing NHC redox catalysis (Scheme 1b). Although proceeding with excellent  selectivity in many examples, this method provided a mixture of Lewis basic isothioureas catalysts, first reported for acyl transfer reactions by Birman and Okamoto, have been applied for the acylative KR of primary, secondary and tertiary alcohols bearing point chirality.