42479-97-0Relevant 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.
Bioinspired, base- and metal-free, mild decarboxylative aldol activation of malonic acid half thioesters under phase-transfer reaction conditions
Bew, Sean P.,Stephenson, G. Richard,Rouden, Jacques,Ashford, Polly-Anna,Bourane, Manuel,Charvet, Agathe,Dalstein, Virginie M. D.,Jauseau, Raphael,Hiatt-Gipson,Martinez-Lozano, Luis A.
, p. 1245 - 1257 (2015/04/22)
Utilizing 'off the shelf' commercially available, cheap, small synthetic molecules that mimic the efficient mediation of important bioreactions utilized by Nature is not only highly sought after but also currently highly topical. This paper details our preliminary efforts at developing a unique base- and metal-free phase-transfer-mediated malonic acid thioester (MAHT) 'activation protocol' that efficiently generates (±)-β-thioesters. Our bioinspired aldol process is exceptionally mild, conducted under near neutral pH reaction conditions, does not require an inert, oxygen-free atmosphere or anhydrous reaction conditions and is highly atom-economic. Exemplifying the utility of our protocol, the synthesis of an array of structurally and functionally diverse (±)-β-hydroxy thioesters equipped with highly prized functionality, i.e., chlorine, bromine, fluorine, nitrile and nitro groups, is reported, as is the diastereoselective potential of this important reaction.
A direct aldol addition of simple thioesters employing soft enolization
Zhou, Guoqiang,Yost, Julianne M.,Coltart, Don M.
, p. 478 - 482 (2007/12/27)
Simple thioesters undergo direct aldol addition to aldehydes in the presence of magnesium bromide-diethyl ether and N,N-diisopropylethylamine using untreated, reagent grade dichloromethane under atmospheric conditions. The reactions proceed extremely rapi
A facile and efficient direct aldol addition of simple thioesters
Yost, Julianne M.,Zhou, Guoqiang,Coltart, Don M.
, p. 1503 - 1506 (2007/10/03)
Simple thioesters undergo direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt using untreated, reagent-grade CH2Cl2 under atmospheric conditions. The reactions proceed extrem
An exceptionally mild catalytic thioester aldol reaction inspired by polyketide biosynthesis
Lalic, Gojko,Aloise, Allen D.,Shair, Matthew D.
, p. 2852 - 2853 (2007/10/03)
This report details our discovery of a new catalytic ester aldol reaction using malonic acid half thioesters (MAHTs) that directly affords β-hydroxythioesters. The reaction is catalyzed by combination of a Cu(II) salt and an amine base, and it can be perf
