66558-04-1Relevant articles and documents
Optically active lithium-alkoxide catalyzed asymmetric reduction of imines with trimethoxyhydrosilane
Nishikori, Hisashi,Yoshihara, Ritsuko,Hosomi, Akira
, p. 561 - 563 (2003)
Optically active lithium alkoxide catalyzed asymmetric reduction of imines with trimethoxhydroysilane in moderate enantioselectivity (up to 72% ee).
Asymmetric hydrogenation of N-tosylimines catalyzed by BINAP-ruthenium(II) complexes
Charette, Andre B.,Giroux, Andre
, p. 6669 - 6672 (1996)
The asymmetric hydrogenation of N-tosylimines was accomplished with a catalytic amount of Ru[(R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl](O2CCH3)2 to afford the corresponding amines in high enantiomeric excesses.
Electrochemical synthesis of sulfonamides in a graphite powder macroelectrode
Galdino, Danilo,Menezes, Paulo H.,Navarro, Marcelo,Vicente, Dmistocles A.
supporting information, p. 5262 - 5266 (2020/09/17)
The electrochemical generation of sulfinyl radicals from commercially available and non-expensive sodium salts of sulfinic acids is described. Electrooxidation reactions were carried out in a graphite powder macroelectrode using an aqueous electrolyte and cavity cell. Further reaction with primary or secondary amines gave the corresponding sulfonamides, a unit present in several biologically active compounds and pharmaceuticals, in good yields.
Nickel-Catalyzed Asymmetric Transfer Hydrogenation and α-Selective Deuteration of N-Sulfonyl Imines with Alcohols: Access to α-Deuterated Chiral Amines
Yang, Peng,Zhang, Li,Fu, Kaiyue,Sun, Yaxin,Wang, Xiuhua,Yue, Jieyu,Ma, Yu,Tang, Bo
supporting information, p. 8278 - 8284 (2020/11/03)
A nickel-catalyzed enantioselective transfer hydrogenation and deuteration of N-sulfonyl imines was developed. Excellent α-selectivity and high deuterium content were achieved by using inexpensive 2-propanol-d8 as a deuterium source. As a highlight, no deuteration of β-C-H and the remote C-H of N-sulfonyl amines occurred, which is hard to achieve using other imines or by hydrogen isotope exchange with D2O. Mechanism studies indicated a stepwise pathway through the [Ni-D] intermediate.
Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex
Seo, Chris S. G.,Tannoux, Thibault,Smith, Samantha A. M.,Lough, Alan J.,Morris, Robert H.
, p. 12040 - 12049 (2019/10/02)
Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.
Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis
Zhao, Xiaohu,Xu, Haiyan,Huang, Xiaolei,Zhou, Jianrong Steve
, p. 292 - 296 (2018/12/13)
Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high-pressure hydrogen gas.
PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
supporting information, p. 2360 - 2364 (2018/05/24)
A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
Highly Efficient One-Pot Synthesis of Novel Propargylamine-Based Sulfonamides by an A3-Coupling Reaction
Abdoli, Morteza,Saeidian, Hamid,Kakanejadifard, Ali
, p. 2473 - 2476 (2016/10/24)
Novel propargylamine-based sulfonamides were synthesized in excellent yields by the copper(I) iodide catalyzed three-component coupling of propargylsulfonamides, morpholine, and aldehydes.
Nickel-catalyzed asymmetric transfer hydrogenation of hydrazones and other ketimines
Xu, Haiyan,Yang, Peng,Chuanprasit, Pratanphorn,Hirao, Hajime,Zhou, Jianrong
, p. 5112 - 5116 (2015/04/27)
We report the use of nickel catalysts for the catalytic transfer hydrogenation of hydrazones and other ketimines with formic acid. Strongly donating bisphosphines must be used to support the catalysts. As in enzymatic catalysis, attractive weak interactio
Palladium-catalyzed intramolecular oxidative coupling involving double C(sp2)-H bonds for the synthesis of annulated biaryl sultams
Laha, Joydev K.,Jethava, Krupal P.,Dayal, Neetu
, p. 8010 - 8019 (2015/03/18)
The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)-H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered ring and analogous sultones are also presented.
