Copper-Nitrene-Catalyzed Desymmetric Oxaziridination/1,2-Alkyl Rearrangement of 1,3-Diketones toward Bicyclic Lactams

Autor: Chang-Sheng Zhang, Fu-Min Zhang, Jin-Xin Zhu, Xiao-Ming Zhang, Yong-Qiang Tu, Ming Yang, Li-Xin Shan, Xue Han, Hong Wang, Wen-Shuo Zhang
Rok vydání: 2021
Předmět:
Zdroj: Angewandte Chemie (International ed. in English). 60(42)
ISSN: 1521-3773
Popis: 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.
Databáze: OpenAIRE