Barbier-Type Reactions of Cyclic Acid Anhydrides and Keto Acids Mediated by an SmI2-(NiI2-Catalytic) System – Preparation of Disubstituted Lactones

✍ Scribed by Fouzia Machrouhi; Elena Pârlea; Jean-Louis Namy

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 209 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199811)1998:11<2431::aid-ejoc2431>3.0.co;2-7

✦ Synopsis

Cyclic acid anhydrides (succinic and glutaric anhydrides and In these reactions the formation of a samarium keto carboxylate intermediate is likely; as a matter of fact, keto some of their derivatives) undergo fast Barbier-type reactions mediated by samarium diiodide in the presence of catalytic carboxylic acids react under similar conditions to also yield disubstituted lactones. It is demonstrated that lactonisation amounts of nickel diiodide (1 mol-% with respect to SmI 2 ), to give disubstituted lactones in high yields. Without NiI 2 no occurs during hydrolysis of the reaction. reaction occurs. Various alkyl and allyl iodides can be used.