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Regio- and Stereoselective Ene and Tandem “Ene-Cycloaddition” Reactions of 2,4-Dioxopentane-3-thione

✍ Scribed by Giuseppe Capozzi; Marco Fragai; Stefano Menichetti; Cristina Nativi

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 300 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199912)1999:12<3375::aid-ejoc3375>3.0.co;2-a

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✦ Synopsis

2,4-Dioxopentane-3-thione 1a reacts as an enophile with ethers or allenes as ene counterparts, the formation of the thiophilic adduct is followed by a fast cycloaddition reaction various allyl derivatives affording thiophilic ene adducts as single regioisomers with high (E) stereoselectivity. Using allyl in which 1a behaves as a diene or a dienophile, respectively.

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