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

Date

2006-06-19

Author

ISLEYEN, Alper
Tanyeli, Cihangir
Doğan, Özdemir

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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.

Subject Keywords

Catalysis, Hydrolysis, Derivatives, Esters, Trans-esterification, organic-solvents

URI

https://hdl.handle.net/11511/42166

Journal

TETRAHEDRON-ASYMMETRY

DOI

https://doi.org/10.1016/j.tetasy.2006.06.001

Collections

Department of Chemistry, Article

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Citation Formats

A. ISLEYEN, C. Tanyeli, and Ö. Doğan, “Kinetic resolution of primary alcohols having remote stereogenic centers: lipase mediated kinetic resolution of (+/-)-3-chloro-3-arylpropanols,” TETRAHEDRON-ASYMMETRY, pp. 1561–1567, 2006, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42166.