LIPASE-CATALYZED KINETIC RESOLUTION OF A SERIES OF ESTERS HAVING A SULFOXIDE GROUP AS THE STEREOGENIC CENTER

Authors
ALLENMARK SG ANDERSSON AC
Citation
Sg. Allenmark et Ac. Andersson, LIPASE-CATALYZED KINETIC RESOLUTION OF A SERIES OF ESTERS HAVING A SULFOXIDE GROUP AS THE STEREOGENIC CENTER, Tetrahedron : asymmetry, 4(11), 1993, pp. 2371-2376
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
11
Year of publication
1993
Pages
2371 - 2376
Database
ISI
SICI code
0957-4166(1993)4:11<2371:LKROAS>2.0.ZU;2-I
Abstract
A series of methyl 2-(alkylsulfinyl)benzoates (alkyl = C1, n-C4, n-C-8 , n-C-12 and n-C-16) was investigated with respect to substrate behavi our and enantioselectivity in a lipase (Candida rugosa)-catalyzed hydr olytic reaction. Although three bonds separate the stereogenic centre and the ester carbonyl group, very high enantioselectivity values (>10 0) could be obtained. It was found that the enzyme consistently showed a strong kinetic preference for the (-)-(S)-enantiomer.