ENDOCYCLIC CLEAVAGE OF GLYCOSIDES - VI - SUBSTITUENT EFFECTS OF THE ALKYLATIVE ENDOCYCLIC CLEAVAGE OF GLYCOSIDES

Authors
OLSSON R BERG U FREJD T
Citation
R. Olsson et al., ENDOCYCLIC CLEAVAGE OF GLYCOSIDES - VI - SUBSTITUENT EFFECTS OF THE ALKYLATIVE ENDOCYCLIC CLEAVAGE OF GLYCOSIDES, Tetrahedron, 54(15), 1998, pp. 3935-3954
Citations number
49
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
15
Year of publication
1998
Pages
3935 - 3954
Database
ISI
SICI code
0040-4020(1998)54:15<3935:ECOG-V>2.0.ZU;2-W
Abstract
A number of pentopyranoside derivatives were treated with Me3Al in ord er to investigate the influence of structural parameters on the methyl group transfer in the endocyclic alkylative cleavage reaction of thes e substrates. A cyclic CH ... O hydrogen bonded model is suggested as an intermediate, which is used to explain the stereoselectivities for different substrates. In several cases the diastereoselectivities were better than 9:1. (C) 1998 Elsevier Science Ltd. All rights reserved.