SOME DIASTEREOSELECTIVE RADICAL REACTIONS OF SUBSTITUTED 1,3-DIOXOLAN-4-ONES

Authors
BECKWITH ALJ CHAI CLL
Citation
Alj. Beckwith et Cll. Chai, SOME DIASTEREOSELECTIVE RADICAL REACTIONS OF SUBSTITUTED 1,3-DIOXOLAN-4-ONES, Tetrahedron, 49(36), 1993, pp. 7871-7882
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
36
Year of publication
1993
Pages
7871 - 7882
Database
ISI
SICI code
0040-4020(1993)49:36<7871:SDRROS>2.0.ZU;2-Q
Abstract
The radical 3, generated (i) from reactions of 5-substituted 2-tert-bu tyl-1,3-dioxolan-4-ones with N-bromosuccinimide, (ii) from related bro mo compounds by reaction with tributylstannane or with allyltributylti n, and (iii) by radical addition to 5-methylene-1,3-dioxolan-4-one, un dergoes carbon-bromine, carbon-hydrogen, and carbon-carbon bond format ion trans to the tert-butyl group with moderate to high diastereoselec tivity