Influence of substituents on enantiomeric ratio in transesterification of racemic C-3 synthons using lipase B from Candida antarctica

The fluorides, chlorides and bromides of 3-halo-1-phenoxy-2-propanol, 3-halo-1-phenylmethoxy-2-propanol and 3-halo-1-(2-phenylethoxy)-2-propanol have been resolved by transesterification with various butanoates as acyl donors in hexane and lipase B from Candida antarctica (Novozyme 435) as catalyst....

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2000-01, Vol.8 (1), p.51-60
Main Authors: Hoff, Bård Helge, Ljones, Liv, Rønstad, Anja, Anthonsen, Thorleif
Format: Article
Language:English
Subjects:
Acyl donor
Candida antarctica lipase B
Enantiomeric ratio
Halohydrins
Transesterification
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Summary:The fluorides, chlorides and bromides of 3-halo-1-phenoxy-2-propanol, 3-halo-1-phenylmethoxy-2-propanol and 3-halo-1-(2-phenylethoxy)-2-propanol have been resolved by transesterification with various butanoates as acyl donors in hexane and lipase B from Candida antarctica (Novozyme 435) as catalyst. The enantiomeric ratio E depended on the hydroxy protecting groups in 1-position and the halogens in 3-position. For some substrates, the enantiomeric ratio was dependent on the acylating agent.
ISSN:1381-1177
1873-3158
DOI:10.1016/S1381-1177(99)00066-1