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Regio‐ and Stereoselective Ene and Tandem “Ene‐Cycloaddition” Reactions of 2,4‐Dioxopentane‐3‐thione
Author(s) -
Capozzi Giuseppe,
Fragai Marco,
Menichetti Stefano,
Nativi Cristina
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199912)1999:12<3375::aid-ejoc3375>3.0.co;2-a
Subject(s) - chemistry , stereoselectivity , cycloaddition , ene reaction , adduct , tandem , stereochemistry , medicinal chemistry , structural isomer , organic chemistry , catalysis , materials science , composite material
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.