13437-79-1Relevant articles and documents
Chiral Bronsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH-Imine Hydrochloride Salts
Wakchaure, Vijay N.,Obradors, Carla,List, Benjamin
supporting information, p. 1707 - 1712 (2020/08/28)
While imines are frequently used substrates in asymmetric Bronsted acid catalysis, their corresponding salts are generally considered unsuitable reaction partners. Such processes are challenging because they require the successful competition of a catalytic amount of a chiral anion with a stoichiometric amount of an achiral one. We now show that enantiopure disulfonimides enable the asymmetric reduction of N-H imine hydrochloride salts using Hantzsch esters as hydrogen source. Our scalable reaction delivers crystalline primary amine salts in great efficiency and enantioselectivity and the discovery suggests potential of this approach in other Bronsted acid catalyzed transformations of achiral iminium salts. Kinetic studies and acidity data suggest a bifunctional catalytic activation mode.
Synthesis method of primary amine hydrochloride
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, (2019/03/09)
The invention discloses a synthesis method of primary amine hydrochloride. According to the synthesis method, in the presence of a gold complex, water and alkyne carry out catalytic hydrolysis to generate ketones, and then ketones and ammonium formate are catalyzed by a rhodium complex to generate primary amine. Compared with a conventional primary amine synthesis method, the synthesis method hasthe advantages that no alkali is added during the reaction process, no side product is generated, the atomic economy is good, the reaction conditions are mild, and the synthesis method has a wide prospect.
Diethylenetriamine-Mediated Direct Cleavage of Unactivated Carbamates and Ureas
Noshita, Megumi,Shimizu, Yuhei,Morimoto, Hiroyuki,Ohshima, Takashi
supporting information, p. 6062 - 6065 (2016/12/09)
Diethylenetriamine is effective for the direct cleavage of unactivated carbamates and ureas without additional reagents and catalysts. Various carbamates and ureas were cleaved to afford products in good yield, and the reactions were not affected by air or moisture. Unique chemoselective cleavage of carbamate and urea in the presence of amides was also achieved.
