Scettri, Arrigo and De Sio, Vincenzo and Villano, Rosaria and Manzo, Patrizia and Acocella, Maria Rosaria (2010) Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases. Tetrahedron Letters, Vol. 51 (28), p. 3658-3661. ISSN 0040-4039. Article.
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The vinylogous aldol-type addition of a dienolsilyl ether, derived from 2,2,6-trimethyl-4H-1,3-dioxin-4-one, showed to occur with complete γ-selectivity by enolate activation promoted by neutral Lewis bases under solvent-free conditions. Moderate to high yields were obtained with aromatic, hetero-aromatic, and aliphatic aldehydes, as well as activated ketones. Under the same conditions and in the absence of catalyst, the first Mukaiyama–Michael addition of the masked acetoacetate ester to α,β-unsaturated aldehydes took place in satisfactory way.
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