alpha ',alpha '-dioxothiones, III Regio- and stereoselective ene and tandem "ene-cycloaddition'' reactions of 2,4-dioxopentane-3-thione

Authors
Capozzi, G Fragai, M Menichetti, S Nativi, C
Citation
G. Capozzi et al., alpha ',alpha '-dioxothiones, III Regio- and stereoselective ene and tandem "ene-cycloaddition'' reactions of 2,4-dioxopentane-3-thione, EUR J ORG C, (12), 1999, pp. 3375-3379
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
12
Year of publication
1999
Pages
3375 - 3379
Database
ISI
SICI code
1434-193X(199912):12<3375:A''IRA>2.0.ZU;2-3
Abstract
2,4-Dioxopentane-3-thione la reacts as an enophile with various allyl deriv atives affording thiophilic ene adducts as single regioisomers with high (E ) stereoselectivity. Using allyl ethers or allenes as ene counterparts, the formation of the thiophilic adduct is followed by a fast cycloaddition rea ction in which la behaves as a diene or a dienophile, respectively.