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

Jhillu S. Yadav; Bhasi V. Subba Reddy

doi:10.1055/s-2002-20968

PAPER

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;

Abstract

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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.

Key words

Ferrier rearrangement - indium reagents - pseudoglycals

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References

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