Photooxygenation of chiral dienol ethers: asymmetric synthesis of alkoxydioxines

Authors
Dussault, PH Han, Q Sloss, DG Symonsbergen, DJ
Citation
Ph. Dussault et al., Photooxygenation of chiral dienol ethers: asymmetric synthesis of alkoxydioxines, TETRAHEDRON, 55(38), 1999, pp. 11437-11454
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
38
Year of publication
1999
Pages
11437 - 11454
Database
ISI
SICI code
0040-4020(19990917)55:38<11437:POCDEA>2.0.ZU;2-N
Abstract
The addition of O-1(2) to chiral dienol ethers provides a new route to alko xydioxines (alkoxyendoperoxides). Depending upon substitution and geometry, the [4+2] cycloaddition is accompanied or even supplanted by [2+2] cycload dition leading to alkene cleavage and/or ene-like reaction leading to allyl ic hydroperoxides. The diastereoselectivity of cycloaddition is ultimately limited by the conformational freedom of the dienol ether substrates. (C) 1 999 Elsevier Science Ltd. All rights reserved.