ENZYMATIC DESYMMETRIZATION OF PROCHIRAL ,3-BIS(ACETOXYMETHYL)BICYCLO[2.2.1]HEPTA-2,5-DIENE AND ,3-BIS(HYDROXYMETHYL)BICYCLO[2.2.1]HEPTA-2,5-DIENE

Authors
RANCHOUX M BRUNEL JM IACAZIO G BUONO G
Citation
M. Ranchoux et al., ENZYMATIC DESYMMETRIZATION OF PROCHIRAL ,3-BIS(ACETOXYMETHYL)BICYCLO[2.2.1]HEPTA-2,5-DIENE AND ,3-BIS(HYDROXYMETHYL)BICYCLO[2.2.1]HEPTA-2,5-DIENE, Tetrahedron : asymmetry, 9(4), 1998, pp. 581-587
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
4
Year of publication
1998
Pages
581 - 587
Database
ISI
SICI code
0957-4166(1998)9:4<581:EDOP,>2.0.ZU;2-O
Abstract
Enzymatic desymmetrization of the title compound 1 is reported using v arious commercially available lipases in hydrolysis and alcoholysis re actions or ester synthesis. In this area, lipase Amano AK (Pseudomonas sp,) proved to be the best lipase whatever the experimental condition s used. The monoacetate product 2 is indifferently obtained with more than 95% enantiomeric excess (ee) as the levorotatory enantiomer 2a or the dextrorotatory one 2b. (C) 1998 Published by Elsevier Science Ltd . All rights reserved.