Synthetic Communications p. 817 - 828 (2004)
Update date:2022-08-04
Topics:
Clososki, Giuliano C.
Costa, Carlos E.
Missio, Lauri J.
Cass, Quezia B.
Comasseto, Joao V.
Lipase-catalyzed lactonization of (2) provides both (R) and (S) enantiomers of 5-phenylselenyltetrahydro-2-furanone (1) in good enantiomeric excess. The kinetic resolution was examined using PPL (Porcine pancreatic lipase), PSL (Amano PS, Pseudomonas sp. lipase), MML (Mucor miehei lipase), CRL (Candida rugosa lipase), CAL-B (Candida Antarctica lipase, type B) and Novozym 435 (immobilized C. antarctica lipase type B) in different solvents. A tributyltin hydride reduction of enantiomerically enriched 1 gave both (R) and (S) enantiomers of S-4-pentanolide (γ-valerolactone).
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