Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases

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• 作者：Arrigo Scettri ; Vincenzo De Sio ; Rosaria Villano ; Patrizia Manzo ; Maria Rosaria Acocella
• 关键词：Mukaiyama ; Mukaiyama– ; Michael ; Dioxinone ; Vinylogous ; Aldol reaction
• 刊名：Tetrahedron Letters
• 出版年：2010
• 出版时间：14 July 2010
• 年：2010
• 卷：51
• 期：28
• 页码：3658-3661
• 全文大小：187 K

文摘

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.