1076238-91-9Relevant academic research and scientific papers
Enantioselective N-H insertion reaction of α-aryl α-diazoketones: An efficient route to chiral α-aminoketones
Xu, Bin,Zhu, Shou-Fei,Zuo, Xiao-Dong,Zhang, Zhi-Chao,Zhou, Qi-Lin
, p. 3913 - 3916 (2014)
A highly enantioselective N-H insertion reaction of α-diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral α-aminoketones, which are versatile building blocks in organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions. Spiro inspiration: A highly enantioselective N-H insertion reaction of α-diazoketones was developed by using cooperative catalysis by dirhodium(II) carboxylates and chiral spiro phosphoric acids. The insertion reaction provides a new access route to diverse chiral α-aminoketones, which are versatile building blocks in the organic synthesis, with fast reaction rates, good yields and high enantioselectivity under mild and neutral conditions.
Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity
Chen, Ching-Nung,Cheng, Wei-Min,Wang, Jian-Kai,Chao, Tzu-Hsuan,Cheng, Mu-Jeng,Liu, Rai-Shung
supporting information, p. 4479 - 4484 (2021/01/21)
This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.
Enantioselective Synthesis of 2,2,3-Trisubstituted Indolines via Bimetallic Relay Catalysis of α-Diazoketones with Enones
Yang, Jian,Ke, Chaoqi,Zhang, Dong,Liu, Xiaohua,Feng, Xiaoming
supporting information, p. 4536 - 4539 (2018/08/07)
An efficient asymmetric intramolecular trapping of ammonium ylides of α-diazoketones with enones to synthesize indoline derivatives was realized. A Rh(II)/chiral N,N′-dioxide-Sc(III) complex bimetallic relay catalytic system was established. A series of optically active 2,2,3-trisubstituted indolines were obtained in high yields (up to 99%), good enantioselectivities (up to 99% ee), and excellent diastereoselectivities (up to >19:1 dr) under mild reaction conditions.
Enantioselective reactions of donor/acceptor carbenoids derived from α-aryl-α-diazoketones
Denton, Justin R.,Davies, Huw M. L.
supporting information; experimental part, p. 787 - 790 (2009/09/06)
The reaction of a variety of α-aryl-α-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh2(S-PTAD)4, generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene by means of carbenoid-induced C-H insertion was also possible with this type of carbenoid.
