ChemInform Abstract: Enantioselective Synthesis of Benzylbutyrolactones from 5-Hydroxyfuran-2(5H)-one. New Chiral Synthons for Dibenzylbutyrolactone Lignans by a Chemoenzymatic Route.

✍ Scribed by Jelle Brinksma; Hanneke van der Deen; Arjan van Oeveren; Ben L. Feringa

• Book ID: 101881008
• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199919121

✦ Synopsis

Enantioselective Synthesis of Benzylbutyrolactones from 5-Hydroxyfuran-2(5H)-one.

New Chiral Synthons for Dibenzylbutyrolactone Lignans by a Chemoenzymatic Route.

-Ongoing interest in lignan chemistry leads to the development of an efficient approach to the chiral acetate (R)-(III). In this process the formed (S)-enantiomer of (I) spontaneously racemized to (±)-(I). It is noteworthy that lipase PS reacts much faster but produces (R)-(III) with decreased enantioselectivity (89% e.e.). The usefulness of such a synthon is shown by the transformation to compounds such as (VI).