Issue 6, 1999

An unexpected allyl-transfer reaction under conditions of Lewis acid- promoted cyclization of homoallylic alcohols with aldehydes

Abstract

The title reaction was observed along with cyclization in the SnCl4-promoted reaction of 2-[3,4,6-tri-O-benzyl-2-deoxy-2- (p-tolylsulfanyl)-β-D-glucopyranosyl]ethanal with pent-4-en-2-ol and this result was interpreted in terms of anchimeric assistance by sulfur to the unusual fragmentation of an intermediate alkoxycarbenium ion.

Article information

Article type
Paper

Mendeleev Commun., 1999,9, 219-221

An unexpected allyl-transfer reaction under conditions of Lewis acid- promoted cyclization of homoallylic alcohols with aldehydes

V. V. Samoshin, I. P. Smoliakova, M. Han and P. H. Gross, Mendeleev Commun., 1999, 9, 219 DOI: 10.1070/MC1999v009n06ABEH001180

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