585529-12-0Relevant articles and documents
Merging Photoredox/Nickel Catalysis for Cross-Electrophile Coupling of Aziridines with Pyridin-1-ium Salts via Dearomatization
Xu, Chong-Hui,Li, Jin-Heng,Xiang, Jian-Nan,Deng, Wei
supporting information, p. 3696 - 3700 (2021/05/04)
Merging photoredox/nickel catalysis enabling the cross-electrophile coupling of aziridines with pyridin-1-ium salts involving dearomatization for the synthesis of β-(1,4-dihydropyridin-4-yl)-ethylamines, especially including bioactive motif-based analogue
Visible-Light-Driven Nitrogen Radical-Catalyzed [3 + 2] Cyclization of Vinylcyclopropanes and N-Tosyl Vinylaziridines with Alkenes
Chen, Jia-Rong,Wu, Ya-Li,Xiao, Wen-Jing,Xu, Shuang-Hua,Zhao, Quan-Qing,Zhou, Xue-Song
, (2020/03/13)
A visible light photoredox-promoted and nitrogen radical catalyzed [3 + 2] cyclization of vinylcyclopropanes and N-tosyl vinylaziridines with alkenes is developed. Key to the success of this process is the use of the readily tunable hydrazone as a nitrogen radical catalyst. Preliminary mechanism studies suggest that the photogenerated nitrogen radical undergoes reversible radical addition to the vinylcyclopropanes and N-tosyl vinylaziridines to enable their ring-opening C-C and C-N bond cleavage and ensuing cyclization with alkenes.
Visible-Light Photoredox-Catalyzed Formal [5 + 1] Cycloaddition of N-Tosyl Vinylaziridines with Difluoroalkyl Halides
Liu, Yantao,Luo, Wen,Wang, Zhenjie,Zhao, Yuxin,Zhao, Jingjing,Xu, Xuejun,Wang, Chaojie,Li, Pan
supporting information, p. 9658 - 9664 (2020/12/21)
A visible-light photoredox-catalyzed formal [5 + 1] cycloaddition of N-tosyl vinylaziridines with difluoroalkyl halides as unique C1 synthons was developed. The procedure provides an efficient and practical method to synthesize diverse pyridines in moderate to good yields. The reaction underwent a radical-initiated kinetically controlled ring-opening of vinylaziridines and involved a key α,β-unsaturated imine intermediate, followed by an E2 elimination, a 6πelectrocyclization, and defluorinated aromatization.
A Bulky Thiyl-Radical Catalyst for the [3+2] Cyclization of N-Tosyl Vinylaziridines and Alkenes
Hashimoto, Takuya,Takino, Kohei,Hato, Kazuki,Maruoka, Keiji
, p. 8081 - 8085 (2016/09/13)
Thiyl-radical-catalyzed cyclization reactions of N-tosyl vinylaziridines and alkenes were developed as a new synthetic method for the generation of substituted pyrrolidines. The key to making this process accessible to a broad range of substrates is the use of a sterically demanding thiyl radical, which prevents the undesired degradation of the catalyst.
The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(I)-Catalyzed Intermolecular Cycloadditions of Vinyl Aziridines and Alkynes
Feng, Jian-Jun,Lin, Tao-Yan,Zhu, Chao-Ze,Wang, Huamin,Wu, Hai-Hong,Zhang, Junliang
supporting information, p. 2178 - 2181 (2016/03/08)
Catalyst-controlled divergent intermolecular cycloadditions of vinylaziridines with alkynes have been developed. By using [Rh(NBD)2]BF4 as the catalyst, a [3 + 2] cycloaddition reaction was achieved with broad substrate scope and high stereoselectivity under mild reaction conditions. Moreover, the chirality of vinylaziridines can be completely transferred to the [3 + 2] cycloadducts. When the catalyst was changed to [Rh(η6-C10H8) (COD)]SbF6, the alternative [5 + 2] cycloadducts were selectively formed under otherwise identical conditions.
Method of producing optically active aziridine compounds and amine compounds
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Page 9-10, (2010/02/08)
An optically active aziridine compound or amine compound is produced by using a specified Ru(salen)(CO) complex as a catalyst, and subjecting a specified olefin to an asymmetric aziridination or amination with a specified arylsulfonyl azide compound.
