Solvent-free Mukaiyama and Mukaiyama-Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases |
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Authors: | Arrigo Scettri Vincenzo De Sio Patrizia Manzo |
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Affiliation: | a Dipartimento di Chimica, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (Salerno), Italy b Istituto di Chimica Biomolecolare del CNR , Traversa La Crucca 3. 07040 Li Punti (Sassari), Italy |
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Abstract: | 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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Keywords: | Mukaiyama Mukaiyama-Michael Dioxinone Vinylogous Aldol reaction |
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