Silylative Kinetic Resolution of Racemic 2,2‐Dialkyl 5‐ and 6‐Membered Cyclic Benzylic Alcohol Derivatives Catalyzed by Chiral Guanidine, (R)‐N‐Methylbenzoguanidine

Abstract

AbstractEfficient silylative kinetic resolution of racemic 2,2‐dialkyl 5‐ and 6‐membered cyclic benzylic alcohols was achieved using diphenylmethylchlorosilane (Ph2MeSiCl) or phenyldimethylchlorosilane (PhMe2SiCl) as a silyl source catalyzed by chiral guanidine. The reaction could be applied to a broad range of 2,2‐dialkyl 1‐indanols with good s‐values, irrespective of the electronic nature of the substituent on the aromatic ring of the substrates and the type of substituent at the C2‐position. In addition, several 2,2‐dimethyl 6‐membered cyclic and heterocyclic alcohols could be adopted in the reaction.magnified image