132868-33-8Relevant articles and documents
Enzymes in Organic Synthesis, 18. Lipase-Catalyzed Asymmetric Alcoholysis of 3-Substituted Pentanedioic Anhydrides
Ozegowski, Ruediger,Kunath, Annamarie,Schick, Hans
, p. 805 - 808 (2007/10/02)
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 >98percent 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 90percent.Key Words: Enzymes / Lipases / Pentanedioic anhydrides / Alcoholysis, asymmetric / Pentanedioates