The Oxidative �� Coupling of Carbonyl Compounds Via the Condensation of Acylated Triazolinedione (PTAD) Ylides With Enolates: A Facile Synthesis of Polyacylated Olefins
Journal of the American Chemical Society
��-Urazolyl ketones are readily oxidized to acylated N-phenyltriazolinedione ylides with tert-butyl hypochlorite. These ylides, usually as generated in situ, undergo condensations with enolate species to form acylated olefins in synthetically useful yields. The ylide derived from deoxybenzoin is sufficiently stable to be isolated and characterized, and displays the same type of condensation chemistry with enolates as do other less stable ylides that must be generated in situ. The tri- and tetraacylolefins produced by this method are susceptible to subsequent Michael addition of enolates. Intramolecular cyclization or basic cleavage of these Michael adducts leads to a variety of interesting secondary products.
R. M. Wilson, A. C. Hengge, A. Ataei, D. M. Ho. “The Oxidative Alpha-Coupling of Carbonyl Compounds Via the Condensation of Acylated Triazolinedione (PTAD) Ylides With Enolates: A Facile Synthesis of Polyacylated Olefins,” J. Am. Chem. Soc., 1991, 113, 7240-7249.