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Regio- and Stereoselective Ene and Tandem “Ene-Cycloaddition” Reactions of 2,4-Dioxopentane-3-thione (1999)

Capozzi, Giuseppe ; Fragai, Marco ; Menichetti, Stefano ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 3375-3379

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Details

ISSN: 1434-193X

Keywords: α,α′-Dioxothiones ; Ene reactions ; Cyclo additions ; Sulfur heterocycles ; Stereoselectivity ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 2,4-Dioxopentane-3-thione 1a reacts as an enophile with various allyl derivatives 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 reaction in which 1a behaves as a diene or a dienophile, respectively.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

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