Organic synthesis with enzymes. 3. TBADH-catalyzed reduction of chloro ketones. Total synthesis of (+)-(S, S)-(cis-6-methyltetrahydropyran-2-yl) acetic acid: a civet …

E Keinan, KK Seth, R Lamed

Index: Keinan, Ehud; Seth, Kamal K.; Lamed, Raphael Journal of the American Chemical Society, 1986 ,  vol. 108,  # 12  p. 3474 - 3480

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Citation Number: 114

Abstract

Abstract: Highly enantioselective reduction of aliphatic chloro ketones catalyzed by Thermoanaerobium brockii alcohol dehydrogenase (TBADH) afforded the corresponding S chloro alcohols, which are new and useful chiral bifunctional building blocks. The synthetic potential of these compounds was illustrated by syntheses of several optically pure cyclic ethers. In particular,(S)-(+)-5-chloropentan-2-01 was used for the total synthesis of (+)-(S+ ...