Influence of electronic factors on palladium-mediated cycloisomerization: a systematic investigation of competitive 5-exo-dig versus 6-endo-dig cyclizations of sugar alkynols

TitleInfluence of electronic factors on palladium-mediated cycloisomerization: a systematic investigation of competitive 5-exo-dig versus 6-endo-dig cyclizations of sugar alkynols
Publication TypeJournal Article
Year of Publication2008
AuthorsRamana, CV, Mallik, R, Gonnade, RG
JournalTetrahedron
Volume64
Issue1
Pagination219-233
Date PublishedJAN
Type of ArticleArticle
ISSN0040-4020
KeywordsC-alkynyl furanose, cycloisomerization, enol ether, Palladium, Spiroketal
Abstract

Pd-mediated cycloisomerization of 3-C-alkynyl-allo- and ribofuranose derivatives was investigated in detail to understand the influence of electronic factors on the regioselectivity in ring closure reaction. The reactions in general are influenced by the electronic nature of the substituent on the alkyne unit. A preference for endo-dig cyclization over exo-dig is noted, if the alkynyl substituent is not sufficiently electron withdrawing, (c) 2007 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2007.10.072
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.645

Divison category: 
Organic Chemistry
Physical and Materials Chemistry