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Stereoselective Synthesis of (E)-4-Alkylidenecyclopent-2-en-1-ones by a Tandem Ring Closure-Michael Addition-Elimination

Roberto Ballini, Giovanna Bosica, Dennis Fiorini, Maria Victoria Gil and Marino Petrini*

*Dipartimento di Scienze Chimiche, UniversitÓ di Camerino, via S. Agostino, 1. I-62032 Camerino, Italy, Email: marino.petriniunicam.it

R. Ballini, G. Bosica, D. Fiorini, M. V. Gil, M. Petrini, Org. Lett., 2001, 3, 1265-1267.

DOI: 10.1021/ol0069352


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Abstract

The reaction of (Z)-1,4-diketones with various functionalized nitroalkanes in the presence of DBU provides 4-alkylidenecyclopent-2-en-1-ones with E selectivity. An intramolecular aldol condensation probably forms a cyclopentadienone intermediate, which reacts with the nitroalkane in a Michael addition-elimination.

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Key Words

cyclopentenones


ID: J54-Y2001