158568-75-3Relevant academic research and scientific papers
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.
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.
Efficient asymmetric transfer hydrogenation of N-sulfonylimines on water
Wang, Lei,Zhou, Qi,Qu, Chuanhua,Wang, Qiwei,Cun, Linfeng,Zhu, Jin,Deng, Jingen
, p. 6500 - 6506 (2013/07/26)
An efficient and green approach for synthesis of optically active amines was developed via asymmetric transfer hydrogenation of N-sulfonyl ketimines catalyzed by the chiral and lipophilic rhodium-amido complex on water. Higher reactivity and enantioselect
Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family
Leverett, Carolyn A.,Cassidy, Michael P.,Padwa, Albert
, p. 8591 - 8601 (2007/10/03)
cis-2-Methyl-6-substituted piperidin-3-ol alkaloids of the Cassia and Prosopis species are readily prepared by a combination of an aza-Achmatowicz oxidative rearrangement and dihydropyridone reduction followed by a stereoselective allylsilane addition to
An efficient preparation of optically active α-furfuryl amide by kinetic resolution using the modified sharpless asymmetric epoxidation reagent
Zhou, Wei-Shan,Lu, Zhi-Hui,Wang, Zhi-Min
, p. 1467 - 1470 (2007/10/02)
Kinetic resolution of α-furfuryl amide was first carried out by using the modified Sharpless asymmetric epoxidation reagent to give the slow-reacting enantiomers, (S)-la-f and (R)-lb,f in high enantioselectivity (90-100% e.e) and high chemical yield (45-5
