62264-41-9Relevant academic research and scientific papers
Copper-Nitrene-Catalyzed Desymmetric Oxaziridination/1,2-Alkyl Rearrangement of 1,3-Diketones toward Bicyclic Lactams
Han, Xue,Shan, Li-Xin,Tu, Yong-Qiang,Wang, Hong,Yang, Ming,Zhang, Chang-Sheng,Zhang, Fu-Min,Zhang, Wen-Shuo,Zhang, Xiao-Ming,Zhu, Jin-Xin
, p. 22688 - 22692 (2021)
Although copper-nitrene has been extensively studied as a versatile active species in various transformations, asymmetric reactions involving copper-nitrene have been limited to the aziridination of olefins. Herein, we report the novel copper-nitrene-catalyzed desymmetric oxaziridination reaction of cyclic diketones with alkyl azides and the subsequent rearrangement of the resulting highly active intermediate, which produces a synthetically challenging chiral bicyclic lactam containing a quaternary carbon center. This procedure not only enriches the copper-nitrene-catalyzed asymmetric reactions, but also provides an alternative strategy to address the inherent challenges of catalytic asymmetric Schmidt reactions. This unique reaction could inspire the investigation of novel copper-nitrene-catalyzed asymmetric transformations and their reaction mechanisms.
