Synthesis 2022(4): 0511-0514
DOI: 10.1055/s-2002-20968
PAPER
© Georg Thieme Verlag Stuttgart · New York

InBr3-Catalyzed Ferrier Rearrangement: An Efficient Synthesis of C-Pseudoglycals

Jhillu S. Yadav*, Bhasi V. Subba Reddy
Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)7160512; e-Mail: yadav@iict.ap.nic.in;
Further Information

Publication History

Received 7 November 2001
Publication Date:
28 July 2004 (online)

Abstract

Glycals react smoothly with silyl nucleophiles such as allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in the presence of a catalytic amount of indium tribromide to give the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high α-selectivity.