THE DIFFERENT BEHAVIOR OF SYN-2,3-DIMETHYLBUTANEDIOIC AND ANTI-2,3-DIMETHYLBUTANEDIOIC ANHYDRIDE IN THE LIPASE-CATALYZED ENANTIOSELECTIVE ALCOHOLYSIS

Authors
OZEGOWSKI R KUNATH A SCHICK H
Citation
R. Ozegowski et al., THE DIFFERENT BEHAVIOR OF SYN-2,3-DIMETHYLBUTANEDIOIC AND ANTI-2,3-DIMETHYLBUTANEDIOIC ANHYDRIDE IN THE LIPASE-CATALYZED ENANTIOSELECTIVE ALCOHOLYSIS, Tetrahedron : asymmetry, 6(5), 1995, pp. 1191-1194
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
5
Year of publication
1995
Pages
1191 - 1194
Database
ISI
SICI code
0957-4166(1995)6:5<1191:TDBOSA>2.0.ZU;2-F
Abstract
The syn- and anti-relationship of the vicinal methyl groups in the 2,3 -dimethylbutanedioic anhydrides 1 and rac-5 has a significant influenc e on the lipase-catalyzed enantioselective alcoholysis with 2-methylpr opanol. For their conversion into the enantiomerically highly enriched monoesters 2 and ent-6 different enzymes are required. Lipase SP 525 (Novo Nordisk) and lipase Amano PS from Pseudomonas cepacia turned out to be the most suitable ones. Remarkably, the (2S,3S)-anti-anhydride ent-5 is alcoholysed with high enantioselectivity to the monoester ent -6, the other enantiomer (5) remains almost unattacked and can be isol ated with an e.e. of 96 %.