Highly enantioselective dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipoprotein lipase preparation

Abstract

The kinetic and dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipase preparation containing lipoprotein lipase, dextrin, and ionic surfactant 1 has been explored. It was found that all the trimethylsilyl-containing substrates were accepted by lipoprotein lipase-dextrin 1 (LPL-D1) with perfect enantioselectivity (E = >200). As a result, the dynamic kinetic resolution of these substrates with LPL-D1 in the presence of a Ru-based racemization catalyst provided single enantiomeric products (>99% ee) with good yields. Furthermore, the dynamic kinetic resolution products were readily desilylated or halodesilylated to yield enantiopure alkyl aryl carbinols. Thus a useful protocol for the highly enantioselective synthesis of alkyl aryl carbinols, particularly those carrying a long alkyl chain (C-6-C-10) has been established. (C) 2015 Elsevier Ltd. All rights reserved.