V. V. Samoshin, I. P. Smoliakova, M. Han, P. H. Gross, “An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes”, Mendeleev Commun., 1999, Volume 9, Issue 6,Pages <nobr>219

This article is cited in 6 papers

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

V. V. Samoshin^a, I. P. Smoliakova^b, M. Han^b, P. H. Gross^a

^a Department of Chemistry, University of the Pacific, Stockton, California, USA
^b Department of Chemistry, University of North Dakota, Grand Forks, North Dakota, USA

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.

Language: English

DOI: 10.1070/MC1999v009n06ABEH001180