1125576-35-3Relevant articles and documents
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, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme
Prier, Christopher K.,Zhang, Ruijie K.,Buller, Andrew R.,Brinkmann-Chen, Sabine,Arnold, Frances H.
, p. 629 - 634 (2017/06/30)
C-H bonds are ubiquitous structural units of organic molecules. Although these bonds are generally considered to be chemically inert, the recent emergence of methods for C-H functionalization promises to transform the way synthetic chemistry is performed. The intermolecular amination of C-H bonds represents a particularly desirable and challenging transformation for which no efficient, highly selective, and renewable catalysts exist. Here we report the directed evolution of an iron-containing enzymatic catalyst - based on a cytochrome P450 monooxygenase - for the highly enantioselective intermolecular amination of benzylic C-H bonds. The biocatalyst is capable of up to 1,300 turnovers, exhibits excellent enantioselectivities, and provides access to valuable benzylic amines. Iron complexes are generally poor catalysts for C-H amination: in this catalyst, the enzyme's protein framework confers activity on an otherwise unreactive iron-haem cofactor.
Catalytic coupling of N-benzylic sulfonamides with silylated nucleophiles at room temperature
Yang, Bai-Ling,Tian, Shi-Kai
supporting information; experimental part, p. 6180 - 6182 (2010/10/20)
In the presence of 2-10 mol% of Tf2NH, a range of N-benzylic sulfonamides smoothly react with allylic, propargylic, benzylic, or hydrido silanes at room temperature via sp3 carbon-nitrogen bond cleavage to afford structurally diverse products in moderate to excellent yields and with high chemo- and regioselectivity.