Solvent-free Mukaiyama and Mukaiyama–Michael vinylogous reactions of a dioxinone-derived silyl enol ether promoted by Lewis bases
A Scettri, V De Sio, R Villano, P Manzo, MR Acocella
Index: Scettri, Arrigo; Sio, Vincenzo De; Villano, Rosaria; Manzo, Patrizia; Acocella, Maria Rosaria Tetrahedron Letters, 2010 , vol. 51, # 28 p. 3658 - 3661
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Citation Number: 8
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 ...
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