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Issue 10, 2016
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Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine

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Abstract

The highly diastereoselective intramolecular [3+2] annulation via the ring-opening of a cyclopropane diester derivative has been developed to construct a dihydroquinolinone scaffold. A series of tricyclic dihydroquinolinones bearing one or two all-carbon quaternary stereogenic centers were obtained in good yields and excellent diastereoselectivities (up to 20 : 1 dr). Moreover, the amide-linking mode shows obviously beneficial effects on the ring-opening of cyclopropane.

Graphical abstract: Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine

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Supplementary files

Article information


Submitted
07 Sep 2015
Accepted
14 Dec 2015
First published
14 Dec 2015

Chem. Commun., 2016,52, 2177-2180
Article type
Communication
Author version available

Amide-assisted intramolecular [3+2] annulation of cyclopropane ring-opening: a facile and diastereoselective access to the tricyclic core of (±)-scandine

J. Xiao, P. Xia, X. Zhang, X. Chen, G. Ou and H. Yang, Chem. Commun., 2016, 52, 2177
DOI: 10.1039/C5CC07485A

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