1226784-41-3Relevant academic research and scientific papers
One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents
Downey, C. Wade,Dixon, Grant J.,Ingersoll, Jared A.,Fuller, Claire N.,MacCormac, Kenneth W.,Takashima, Anna,Sediqui, Rohina
supporting information, (2019/10/14)
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.
The Mukaiyama aldol and Mukaiyama-Michael reactions promoted by commercially available molecular sieves
Anada, Masahiro,Washio, Takuya,Watanabe, Yudai,Hashimoto, Shunichi
experimental part, p. 1489 - 1503 (2010/10/20)
The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 molecular sieves (4 MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles
