Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (+/-)-3-chloro-3-arylpropanols

ISLEYEN A., Tanyeli C., Dogan O.

TETRAHEDRON-ASYMMETRY, vol.17, no.10, pp.1561-1567, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 17 Issue: 10
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tetasy.2006.06.001
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1561-1567
  • Middle East Technical University Affiliated: Yes

Abstract

Kinetic resolutions of (+/-)-3-chloro-3-arylpropanols by lipase mediated acetylation are described for the first time. Acetylation with CCL provided the best enantioselectivity amongst the enzymes used. Enantiomerically enriched products were obtained with up to 78% ee after two successive lipase-catalyzed acetylations. Different substituents on the aromatic ring and bromide, instead of chloride, on the substrates were found to have no drastic influence on the enantioselectivity of the reaction. (c) 2006 Elsevier Ltd. All rights reserved.