72178-59-7Relevant academic research and scientific papers
Route to Highly Substituted Pyridines
Hilf, Justin A.,Holzwarth, Michael S.,Rychnovsky, Scott D.
, p. 10376 - 10382 (2016/11/17)
Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Hosomi-Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.
Asymmetric direct michael addition of acetophenone to α,β- unsaturated aldehydes
Li, Wenjun,Wu, Wenbin,Yang, Juanjuan,Liang, Xinmiao,Ye, Jinxing
experimental part, p. 1085 - 1091 (2011/05/14)
The asymmetric direct Michael addition of ,-unsaturated aldehydes with acetophenone catalyzed by a Jorgensen-Hayashi-catalyst in methanol was developed and the corresponding Michael products of -keto aldehydes could be afforded in up to 82% yield and 98% ee. Georg Thieme Verlag Stuttgart.
An environmentally friendly Mukaiyama aldol reaction catalyzed by a strong Bronsted acid in solvent-free conditions
Barbero, Margherita,Bazzi, Stefano,Cadamuro, Silvano,Dughera, Stefano,Magistris, Claudio,Smarra, Alessandra,Venturello, Paolo
experimental part, p. 2192 - 2197 (2011/04/26)
o-Benzenedisulfonimide, a new strong bench-stable Bronsted acid, has been shown to efficiently catalyze the Mukaiyama aldol reaction of aldehydes or dimethyl acetals with silyl enol ethers under mild solvent-free reaction conditions.
A tertiary amine as a hydride donor: Trichlorosilyl triflate-mediated conjugate reduction of unsaturated ketones
Kotani, Shunsuke,Osakama, Kazuki,Sugiura, Masaharu,Nakajima, Makoto
supporting information; experimental part, p. 3968 - 3971 (2011/09/16)
Bulky tertiary amines, especially dicyclohexylisobutylamine, smoothly reduced α,β-unsaturated ketones in the presence of trichlorosilyl triflate to give the corresponding saturated ketones in excellent yields. Isotope-labeling studies revealed that an α-hydrogen of the amine was transferred to the enones during reduction.
An unexpected diethyl azodicarboxylate-promoted dehydrogenation of tertiaryamine and tandem reaction with sulfonyl azide
Xu, Xiaoliang,Li, Xiaonian,Ma, Lei,Ye, Ning,Weng, Bojie
supporting information; experimental part, p. 14048 - 14049 (2009/03/11)
It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives. Copyright
A novel carbocationic species paired with tetrakis(pentafluorophenyl)borate anion in catalytic aldol reaction
Mukaiyama, Teruaki,Yanagisawa, Manabu,Iida, Daisuke,Hachiya, Iwao
, p. 606 - 607 (2007/10/03)
The aldol reaction of several aldehydes with silyl enol ethers proceeded smoothly to give the corresponding aldols in good to high yields at -78 °C by using 1.0 mol% of a novel cationic species with tetrakis(pentafluorophenyl)borate anion.
