STEREOSELECTIVE SYNTHESIS OF C-GLYCOSIDES WITH A GLYCOSYL DIANION

Authors
WITTMAN V KESSLER H
Citation
V. Wittman et H. Kessler, STEREOSELECTIVE SYNTHESIS OF C-GLYCOSIDES WITH A GLYCOSYL DIANION, Angewandte Chemie, International Edition in English, 32(7), 1993, pp. 1091-1093
Citations number
47
Categorie Soggetti
Chemistry
Journal title
Angewandte Chemie, International Edition in English → ACNP
ISSN journal
05700833
Volume
32
Issue
7
Year of publication
1993
Pages
1091 - 1093
Database
ISI
SICI code
0570-0833(1993)32:7<1091:SSOCWA>2.0.ZU;2-Y
Abstract
No elimination of the functional group at position 2 occurs when the d ilithio compound 1 reacts with a range of electrophiles ''E+'', for ex ample aldehydes and methyl iodide, to give alpha-C-glucosides 2. Thus the flexible concept of C-elongation of pyranoses by umpolung at the a nomeric center may be used for the direct synthesis of the 2-hydroxy c ompounds.