ISSN:
0170-2041
Keywords:
Enzymes
;
Lipases
;
Pentanedioic anhydrides
;
Alcoholysis, asymmetric
;
Pentanedioates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The influence of several enzymes, alcohols, and solvents on the stereochemical outcome of the asymmetric alcoholysis of 3-substituted pentanedioic anhydrides was investigated. The alcoholysis of 3-acetoxypentanedioic anhydride (5a) in diethyl ether with 2-methylpropanol afforded the (3S)-monoester (S)-6a with an enantiomeric excess of 〉 98% when the lipase from Candida sp. 382 was used as the enzyme. Under the same conditions, 3-methoxypentanedioic anhydride (5c) was converted by the lipase of Pseudomonas cepacia (Amano PS) into the (3R)-monoester (R)-6c with an e.e. of 90%.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301126
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