Highly diastereoselective radical addition-cyclization strategy: facile synthesis of substituted furans

Authors
Sibi, MP Rheault, TR Miyabe, H Patil, K Jasperse, CP
Citation
Mp. Sibi et al., Highly diastereoselective radical addition-cyclization strategy: facile synthesis of substituted furans, CR AC S IIC, 4(7), 2001, pp. 581-584
Citations number
21
Categorie Soggetti
Chemistry
Journal title
COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE
ISSN journal
13871609 → ACNP
Volume
4
Issue
7
Year of publication
2001
Pages
581 - 584
Database
ISI
SICI code
1387-1609(200107)4:7<581:HDRASF>2.0.ZU;2-2
Abstract
A novel strategy is described in which an intermolecular carbon-centered ra dical addition to a beta -oxygenated acceptor followed by intramolecular cy clization leads to the formation of 2,3,4- and 2,3,4,5-substituted furan ri ngs. Excellent levels of 2,4-trans selectivity are observed in accordance w ith the Beckwith-Houk model for selectivity in 5-exo radical cyclizations. (C) 2001 Academie des sciences / Editions scientifiques et medicales Elsevi er SAS.