Inverse Electron Demand Hetero Diels–Alder Reactions of Solid Supported α-Acilthiones

Abstract

A solid supported dienic α,α′-dioxothione, obtained from the corresponding resin-linked β-chetoester, is able to react with vinyl ethers to give chemo- and regiospecifically the expected oxathiin cycloadducts. Trans-esterification allowed a quantitative and very clean cleavage of the products from the solid support.

Keywords:

• Diels–alder reactions
• dioxothione
• oxathiins
• solid phase synthesis

Acknowledgments

Work was carried out in the framework of the National Project “Stereoselezione in Sintesi Organica. Metodologie ed Applicazioni” and supported by the MIUR (Ministero Istruzione Università e Ricerca) and by the University of Firenze.