Practical radical cyclisations leading to the construction of near-stereopure quaternary carbon stereogenic centres

Authors
McCague, R Pritchard, RG Stoodley, RJ Williamson, DS
Citation
R. Mccague et al., Practical radical cyclisations leading to the construction of near-stereopure quaternary carbon stereogenic centres, CHEM COMMUN, (24), 1998, pp. 2691-2692
Citations number
12
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
24
Year of publication
1998
Pages
2691 - 2692
Database
ISI
SICI code
1359-7345(199812):24<2691:PRCLTT>2.0.ZU;2-5
Abstract
The 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl auxiliary is effective in directing bromopropargyloxy additions to the olefinic bonds of vinylogous e sters/carbonates; in the presence of AIBN and 1-ethylpiperidinium hypophosp hite, the adducts undergo highly stereoselective reductive radical cyclisat ions in which quaternary carbon stereogenic centres are generated.