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