Novozyme 435 lipase mediated enantioselective kinetic resolution: a facile method for the synthesis of chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol derivatives

摘要

Vinyl 2-chloroacetate was used as an efficient acyl donor for enantioselective acylation of racemic 1,2,3,4-tetrahydroquinolin-4-ols and 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ols with Novozyme 435 lipase. Two enantiocomplimentary tetrahydroquinolin-4-ol or tetrahydro-1H-benzo[b]azepin-5-ol derivatives could be smoothly obtained in good to excellent yields and ee values at the same time. Noteworthily, large scale preparation experiment was also demonstrated when amplified the reaction system to 10 g scale experiment, and products were obtained with high yields and ee values. (C) 2015 Elsevier Ltd. All rights reserved.