197852-01-0Relevant academic research and scientific papers
Br?nsted Base-Mediated Regio- and Stereoselective trans-Silaboration of Propargylamides: Access to 1,2-Vinylborasilanes
Fritzemeier, Russell,Santos, Webster L.
, p. 15534 - 15537 (2017)
A facile method for the preparation of β-boryl-α-silyl aryl acrylamides using phenyllithium, dimethylphenylsilylpinacolborane, and propargylamides is reported. A key feature of this transition metal-free reaction is the Br?nsted base deprotonation of aryl secondary propargylamide to produce a Lewis base that activates the B?Si bond, which is followed by a sequential intramolecular α-silylation-trans-β-borylation. The reaction proceeds in complete regio- and stereoselectivity. A wide variety of N- and aryl-substituted propargylamides afford trans-1,2-vinylborasilanes in high yield. The vicinal borasilane products undergo a variety of subsequent chemoselective transformations.
Synthesis and Characterization of New Boron Compounds Using Reaction of Diazonium Tetraphenylborate with Enaminoamides
Bertolasi, Valerio,Li, Bing-Han,Marek, Luká?,Sedlák, Milo?,Socha, Lubo?,Svoboda, Jan,Svobodová, Markéta
, (2022/01/11)
A family of oxazaborines, diazaborinones, triazaborines, and triazaborinones was prepared by reaction of polarized ethylenes, such as β-enaminoamides, with 4-methylbenzenediazo-nium tetraphenylborates. The reaction conditions (stirring in CH2Cl2 at room temperature (Method A) or stirring with CH3COONa in CH2Cl2 at room temperature (Method B) or refluxing in the CH2Cl2/toluene mixture (Method C)) controlled the formation and relative content of these compounds in the reaction mixtures from one to three products. Substituted oxazaborines gradually rearranged into diazaborinones at 250 °C. The prepared compounds were characterized by1H NMR,13C NMR, IR, and UV–Vis spectroscopy, HRMS, or microanalysis. The structure of individual compounds was confirmed by11B NMR,15N NMR, 1D NOESY, and X-ray analysis. The mechanism of reaction of enaminoamides with 4-methylbenzenediazonium tetraphenylborate was proposed.
The synthesis of a chiral fluoxetine intermediate by catalytic enantioselective hydrogenation of benzoylacetamide
Huang, Hsiang-Ling,Liu, Lee Tai,Chen, Shyh-Fong,Ku, Hao
, p. 1637 - 1640 (2007/10/03)
In the presence of a chiral BINAP-ruthenium(II) catalyst, asymmetric hydrogenation of β-keto propanoic acid N-methyl amide under 200 psi of hydrogen pressure furnished the corresponding 3-hydroxypropanoic acid N- methyl amide as the single enantiomer. The
