Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of gamma-hydroxycyclohexenones

Authors
Ochoa, ME Arias, MS Aguilar, R Delgado, F Tamariz, J
Citation
Me. Ochoa et al., Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one as a Diels-Alder ketene equivalent for the synthesis of gamma-hydroxycyclohexenones, TETRAHEDRON, 55(51), 1999, pp. 14535-14546
Citations number
66
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
51
Year of publication
1999
Pages
14535 - 14546
Database
ISI
SICI code
0040-4020(199912)55:51<14535:CO3AAD>2.0.ZU;2-J
Abstract
A short and regioselective synthesis of gamma-hydroxycyclohexenones is desc ribed, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of t he alpha-acetylcyclohexenol derivative, obtained by hydrolysis of the cyclo adducts, led to the corresponding gamma-hydroxycyclohexenones in moderate o verall yields. Evidence of the mechanism is provided. (C) 1999 Elsevier Sci ence Ltd. All rights reserved.