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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 24, Number 9
BKCSDE 24(9)
September 20, 2003 

Lipase-catalyzed Remote Kinetic Resolution of Quaternary Carbon-containing Alcohols and Determination of Their Absolute Configuration
Dai Sig Im, Chan Seong Cheong, So Ha Lee
Chiral tertiary nitriles, Lipase, Enantioselective, Resolution
The quaternary carbon-containing alcohols (1-6) were resolved enantioselectively by various lipases such as PFL (Pseudomonas fluorescens lipase), LAK (Pseudomonas fluorescens lipase), CRL (Candida rugosa lipase) and PCL (Pseudomonas cepacia lipase). The enzymatic resolution of racemic alcohol (±)-2 gave the excellent enantioselectivity in favor of (S)-2d in 99% ee, while those of the racemic alcohols (1, 3, 4, 5 and 6) gave the resolved alcohols with moderate to good enantioselectivity. Also, their absolute configurations were determined by chemical transformation to the known compounds.
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