FORMATION OF SOME OXYGEN-CONTAINING HETEROCYCLES BY RADICAL CYCLIZATION - THE STEREOCHEMICAL INFLUENCE OF ANOMERIC EFFECTS

Authors
BECKWITH ALJ PAGE DM
Citation
Alj. Beckwith et Dm. Page, FORMATION OF SOME OXYGEN-CONTAINING HETEROCYCLES BY RADICAL CYCLIZATION - THE STEREOCHEMICAL INFLUENCE OF ANOMERIC EFFECTS, Journal of organic chemistry, 63(15), 1998, pp. 5144-5153
Citations number
77
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
15
Year of publication
1998
Pages
5144 - 5153
Database
ISI
SICI code
0022-3263(1998)63:15<5144:FOSOHB>2.0.ZU;2-Q
Abstract
The influence of the anomeric effect on radical cyclization has been e xamined by determining the stereochemical outcome of the ring closure of 10 suitably substituted radicals. The stereochemistry of the produc ts formed from the acyclic precursors 4a-f indicates that for suitably constituted radicals anomeric interactions stabilize pseudoaxially su bstituted transition structures 14 thus affording products with stereo chemistry the reverse of that normally observed.