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Enzymes in organic synthesis, 25. Lipase-catalyzed sequential esterification of (±)-2-methylbutanedioic anhydride — a biocatalytical access to an enantiomerically pure 1-monoester of (S)-2-methylbutanedioic acid

✍ Scribed by Ozegowski, Rüdiger ;Kunath, Annamarie ;Schick, Hans

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 462 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1995199509237

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✦ Synopsis

Abstract

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 LiBH~4~ to (S)‐3‐methylbutan‐4‐olide (ent‐10), a versatile chiral intermediate.

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## Abstract (±)‐__anti__‐2,4‐Dimethylpentanedioic anhydride (__rac__‐1) was converted in good yields and with high enantiomeric excess by an enzyme‐catalyzed sequential esterification into the (2__R__,4__R__)‐monoester 2 and the (2__S__,4__S__)‐diester __ent__‐3. Best results were obtained with Nov