Process for preparing optically active alpha-hydroxyalkene deriv

Details Process for preparing optically active alpha-hydroxyalkene deriv Process for preparing optically active alpha-hydroxyalkene deriv

1994-09-26

1997-06-10

Naff, David M.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435135, 435157, C12P 762, C12P 704, C12P 4100

Patent

active

056375000

ABSTRACT:
A process for preparing optically active 1-substituted-3-hydroxy-1-butene or its derivatives of formula (II) or (III) ##STR1## is disclosed. The process comprises treating an ester derivative of racemic 1-substituted-3-hydroxy-1-butene of formula (I), ##STR2## wherein R.sub.1 is a substituted or unsabstituted alkyl, aryl, alkoxy, or aryloxy group, and R.sub.2 is a hydrogen atom, halogen atom, an alkyl, aryl, alkoxy or aryloxy group, or a substituted or unsabstituted alkylsulfonyloxy, arylsulfonyloxy, alkylthio, or arylthio group. The process can produce a desired optically active alcohol or acyl-protected compound at a high yield and a high selectivity under mild conditions by the treatment of the substrate with a lipase. In particular, when R.sub.1 =methyl and R.sub.2 =halogen or phenylthio, use of Lipase AK, P-30 or K-10 gives high enantiomeric purity.

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