FORMATION OF HIGHLY SUBSTITUTED CYCLOPENTANES FROM RADICAL AND ANIONIC MICHAEL CYCLIZATIONS OF ALPHA-IODO-GAMMA-LACTONES AND ALPHA-IODO-DELTA-LACTONES

Authors
HSIA KY WARD P LAMONT RB LILLEY PMD WATKIN DJ FLEET GWJ
Citation
Ky. Hsia et al., FORMATION OF HIGHLY SUBSTITUTED CYCLOPENTANES FROM RADICAL AND ANIONIC MICHAEL CYCLIZATIONS OF ALPHA-IODO-GAMMA-LACTONES AND ALPHA-IODO-DELTA-LACTONES, Tetrahedron letters, 35(27), 1994, pp. 4823-4826
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
27
Year of publication
1994
Pages
4823 - 4826
Database
ISI
SICI code
0040-4039(1994)35:27<4823:FOHSCF>2.0.ZU;2-2
Abstract
alpha-Iodos-delta- and -gamma-hexonolactones with alpha,beta-unsaturat ed esters developed from C-6 undergo both tributyltin hydride-induced radical and base catalysed anionic Michael cyclisations to form bicycl ic lactones with very highly substituted homochiral cyclopentanes. The delta-lactones give cyclopentane products in which adjacent carbon su bstituents on the cyclopentane ring are cis to each other, whereas gam ma-lactones give cyclopentanes in which the carbon chains are trans.