Hafnium(IV) triflate as a highly efficient catalyst for Ferrier rearrangement of O- and S-nucleophiles with glycals. Issue 25 (22nd June 2016)

• Record Type: Journal Article
• Authors: Liu, Yonghui; Song, Tianbang; Meng, Weijia; Xu, Yun; Wang, Peng George; Zhao, Wei
• Is Part Of: Tetrahedron letters. Volume 57:Issue 25(2016)
• Page Start: 2758
• Page End: 2762
• Publication Date: 2016-06-22
• Subjects: Hafnium(IV) triflate -- 3, 4, 6-Tri-O-acetyl-d-glucal -- Hexa-O-acetyl-d-lactal -- Ferrier rearrangement -- 2, 3-Unsaturated glycosides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.026
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A novel Hf(OTf)4 -catalyzed Ferrier rearrangement. Both mono- and disaccharide derived glycal as the substrates. The efficient and stereoselectivity construction of 2, 3-unsaturated O - and S -glycosides. Abstract: A highly efficient method to afford 2, 3-unsaturated glycosides was described. In the presence of Hafnium(IV) triflate, a variety of 2, 3-unsaturated- O - and S -glycosides have been obtained by stereoselective glycosylation of 3, 4, 6-tri- O -acetyl-d -glucal and hexa- O -acetyl-d -lactal with various acceptors in good isolated yields.