Functionalization of carboxylic anhydrides at α-carbon with hypervalent iodine reagents: one-pot conversion of anhydrides to 2-sulfonyloxycarboxylate esters

✍ Scribed by Jeffrey M Goff; Michael W Justik; Gerald F Koser

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 84 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01028-0

✦ Synopsis

The treatment of carboxylic anhydrides with iodine(III) sulfonate reagents at ca. 100°C and esterification of the reaction mixtures with MeOH/TsOH•H 2 O affords 2-sulfonyloxycarboxylate esters. This is consistent with enolic behavior in the anhydrides.