Steric control in pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization

TitleSteric control in pd-mediated cycloisomerization of sugar alkynols: documentation of a rare allylic epimerization
Publication TypeJournal Article
Year of Publication2007
AuthorsRamana, CV, Patel, P, Gonnade, RG
JournalTetrahedron Letters
Volume48
Issue27
Pagination4771-4774
Date PublishedJUL
Type of ArticleArticle
KeywordsBis-Homopropargylic Alcohols; Oriented Organic-Synthesis;Nucleophilic-Attack; Room-Temperature; Palladium; Chemistry; Heterocycles;Complexes; Transformations; Sonogashira
Abstract

Pd-mediated cycloisomerization of C3-alkynylated glucofuranosyl derivatives revealed a dominance of steric factors over electronic factors. However, the intermediate glycals were epimerized prior to the ketalization and afforded the more stable cis-fused bicyclic ketals. (c) 2007 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetlet.2007.04.133
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.347

Divison category: 
Organic Chemistry