Chemoenzymic synthesis of chiral furan derivatives: useful building blocks for optically active structures

DG Drueckhammer, CF Barbas III…

Index: Drueckhammer, Dale G.; Barbas, Carlos F.; Nozaki, Kenji; Wong, Chi-Huey; Wood, Cynthia Y.; Ciufolini, Marco A. Journal of Organic Chemistry, 1988 , vol. 53, # 8 p. 1607 - 1611

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Citation Number: 90

Abstract

Practical procedures have been developed for the enantioselective reduction of 2. acetylfuran (6a) and 2-(trifluoroacety1) furan (6b) to the corresponding carbinols (S)-1 and 7b with 88-90% ee using Thermoanaerobium brockii alcohol dehydrogenase coupled with an NADPH regeneration system. Kinetic resolution of racemic (S)-1 via lipase-catalyzed esterification, followed by cholesterol esterase or lipase-catalyzed hydrolysis of the ester ...