Synthesis of vinylic C-glycosides from telluroglycosides. Addition of photochemically and thermally generated glycosyl radicals to alkynes

Authors
Yamago, S Miyazoe, H Yoshida, J
Citation
S. Yamago et al., Synthesis of vinylic C-glycosides from telluroglycosides. Addition of photochemically and thermally generated glycosyl radicals to alkynes, TETRAHEDR L, 40(12), 1999, pp. 2343-2346
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
12
Year of publication
1999
Pages
2343 - 2346
Database
ISI
SICI code
0040-4039(19990319)40:12<2343:SOVCFT>2.0.ZU;2-N
Abstract
Glycosyl radicals generated from telluroglycosides react with a variety of alkynes to give the corresponding vinylic C-glycosides in good to excellent yields. The reaction takes place in an atom transfer manner to form vinyl telluride, and the resulting C-Te bond is transmetalated to the C-Zn bond w ith Et2Zn or reduced to the C-H bond with tributyltin hydride. (C) 1999 Els evier Science Ltd. AII rights reserved.