ChemInform Abstract: Direct Indium-Promoted Preparation of α-Methylene-γ-lactones from 2-(Bromomethyl)acrylic Acid and Carbonyl Compounds.

✍ Scribed by Prabir K. Choudhury; Francisco Foubelo; Miguel Yus

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 35 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199951114

✦ Synopsis

Direct Indium-Promoted Preparation of α-Methylene-γ-lactones from 2-(Bromomethyl)acrylic Acid and Carbonyl Compounds.

-Indium-promoted reaction of various carbonyl compounds (II), (IV), (VI), and (VIII) with the title bromomethylacrylic acid (I) under mild conditions provides a versatile access to α-methylene-γ-lactones (III), (V), (VII), and (IX)/(X), respectively. A wide variety of carbonyl compounds such as steric hindered aldehydes or ketones as well as steroid ketones is tolerated. With α,β-unsaturated aldehyde (IIa), the reaction proceeds with absolute chemoselectivity at the carbonyl group. For dicarbonyl compounds like (VIII), mono-or bislactones can be obtained by varying the amount of bromomethylacrylic acid.