Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime

Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime
Qian Zhang, Mengru Zhang, Baozhen Sun, Shuang Liu, Tingting Zhou, Mingzhu Liu, Jinbo Zhao, Zhanyu Li
We report realization of the first enantioselective Cope-type hydroamination of oximes for asymmetric nitrone synthesis. The ligand promoted asymmetric cyclopropene “hydronitronylation” process employs a Cu-based catalytic system and readily available starting materials, operates under mild conditions and displays broad scope and exceptionally high enantio- and diastereocontrol. Preliminary mechanistic studies corroborate a CuI-catalytic profile featuring an olefin metalla-retro-Cope aminocupration process as the key C–N bond forming event. This conceptually novel reactivity enables the first example of highly enantioselective catalytic nitrone formation process and will likely spur further developments that may significantly expedite chiral nitrone synthesis.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06523

DOI: 10.1021/jacs.7b06523

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