Amberlyst 15–Catalyzed Efficient Synthesis of 2,3‐Unsaturated Glycosides via Ferrier Rearrangement for Glycal

Abstract

Amberlyst 15 serves as an inexpensive, effective, and environmentally friendly catalyst in converting 3,4,6‐tri‐O‐acetyl‐D‐glucal (1) into 2,3‐unsaturated O‐ and S‐glycosides via Ferrier rearrangement in moderate to excellent yields with high α selectivity.

Keywords:

• Amberlyst 15
• Ferrier rearrangement
• glycal
• glycosidation
• 2,3‐unsaturated glycoside

Acknowledgment

We are grateful to the National Natural Science Foundation of China (No. 30300434) and the Outstanding Youth Foundation of Sichuan Province, China (No. 04ZQ026‐039) for financial support of this work.