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

Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with α-Diazoacetamides Catalyzed by Silver Phosphate

Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with α-Diazoacetamides Catalyzed by Silver Phosphate
Hiroki Nakayama, Tetsuhiro Nemoto, Shingo Harada, Masato Kono
We report asymmetric dearomatization of phenols using Ag carbenoids from α-diazoacetamides. The Ag catalyst promoted intramolecular dearomatization of phenols, whereas a Rh or Cu catalyst caused C–H insertion and a Büchner reaction. Studies indicated Ag carbenoids have a carbocation-like character, making their behavior and properties unique. Highly enantioselective transformations using Ag carbenoids have not been reported. We achieved a Ag carbenoid-mediated chemo- and highly enantioselective phenol dearomatization with substrate generality for the first time.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04813

DOI: 10.1021/jacs.7b04813

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