EFFICIENT APPLICATION OF LIPASE-CATALYZED TRANSESTERIFICATION TO THE RESOLUTION OF GAMMA-HYDROXY KETONES

Authors
CROTTI P DIBUSSOLO V FAVERO L MINUTOLO F PINESCHI M
Citation
P. Crotti et al., EFFICIENT APPLICATION OF LIPASE-CATALYZED TRANSESTERIFICATION TO THE RESOLUTION OF GAMMA-HYDROXY KETONES, Tetrahedron : asymmetry, 7(5), 1996, pp. 1347-1356
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
5
Year of publication
1996
Pages
1347 - 1356
Database
ISI
SICI code
0957-4166(1996)7:5<1347:EAOLTT>2.0.ZU;2-F
Abstract
(+/-)-trans-2-(Benzoylmethyl)-1-cyclohexanol 4, a gamma-hydroxy ketone (gamma-HK) obtained from the Sc(OTf)(3)-catalyzed addition reaction o f lithium enolate 1 with cyclohexene oxide 2, was very efficiently res olved into (+)-(1S,2R)-4 and acetate (-)-(1R,2S)-6 [ee >99% for both ( +)-4 and (-)-6] by supported lipase PS-catalyzed enantioselective tran sesterification. The enantioselective Sc(OTf)(3)-catalyzed addition of enolate 1 to propene oxide (+)-(R)-3 and (-)-(S)-3 is also described. Copyright (C) 1996 Elsevier Science Ltd