Organic Letters
Organic Letters
5 years ago

Synthesis of Octahydro- and Decahydroquinolines by a One-Pot Cascade Reaction of Tetrasubstituted Enecarbamate

Synthesis of Octahydro- and Decahydroquinolines by a One-Pot Cascade Reaction of Tetrasubstituted Enecarbamate
Tomohiro Kurose, Chihiro Tsukano, Yoshiji Takemoto
A transition-metal-catalyzed cyclopropanation followed by ring opening was investigated for the synthesis of octahydroquinolines 4 and decahydroquinolines 5 having a quaternary carbon center at the angular position, which are core structures of the fawcettimine-type alkaloids. A tandem reaction was also established for the synthesis of decahydroquinolines 5 and the tricyclic compound 6 through an iminium ion intermediate, readily produced by acidic treatment of cyclopropane 2.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02122

DOI: 10.1021/acs.orglett.7b02122

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