ISSN:
0947-3440
Keywords:
Enzymes
;
Butanedioic anhydride, 2-methyl-
;
Alcoholysis, enantio- and regioselective
;
Esterification, enantioselective
;
(S)-3-Methylbutan-4-olide
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The preparation of enantiomerically pure 1-(2-methylpropyl) 4-hydrogen (S)-2-methylbutanedioate (ent-3) by an enzyme-catalyzed sequential esterification of (±)-2-methylbutanedioic anhydride (rac-1) demands two different enzymes. Lipozyme, a lipase from Mucor miehei, was used for the alcoholysis of rac-1 to a mixture of the isomeric monoesters 2/ent-2 and 3/ent-3, whereas Novozym 435, a lipase from Candida antarctica, was required for the enantioselective conversion of a mixture of 3 and ent-3 into the easily separable neutral diester 4 and the acidic monoester ent-3, which thus was obtained in a yield of 26% with an enantiomeric excess of 99%. ent-3 was reduced by LiBH4 to (S)-3-methylbutan-4-olide (ent-10), a versatile chiral intermediate.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199509237
Permalink