4.8 Article

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

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 42, 页码 22688-22692

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107909

关键词

bicyclic lactams; chiral copper-nitrene; oxaziridination; rearrangement reaction; Schmidt reaction

资金

  1. NSFC [21502080, 21772019, 21772076, 21871117, 91956203, 21971095]
  2. 111 Program of MOE
  3. MOST [2018ZX09711001-005-002]
  4. STCSM [19JC1430100]
  5. [lzujbky-2020-ct01]

向作者/读者索取更多资源

A novel copper-nitrene-catalyzed desymmetric oxaziridination reaction was reported, producing a synthetically challenging chiral bicyclic lactam. This enriches the asymmetric reactions involving copper-nitrene and provides an alternative strategy for addressing the challenges of catalytic asymmetric Schmidt reactions. This unique reaction could inspire further investigation into novel copper-nitrene-catalyzed asymmetric transformations and their reaction mechanisms.
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.

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