Enzymatic Resolution of 5‐Phenylselanyltetrahydro‐2‐furanone. Enantioselective Preparation of (R) and (S)‐γ‐Valerolactone

Abstract

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).

Keywords:

• γ‐Valerolactone
• 5‐Phenylselenyltetrahydro‐2‐furanone
• Porcine pancreatic lipase

Acknowledgments

The authors thank FAPESP and CNPq for support and Amano Pharmaceutical Co. and Novozymes Inc. for their generous gifts of lipases. Authors also thank Prof. Liliana Marzorati for critical revision of this article.