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Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines

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Abstract

The first enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines was realized using a chiral phosphoric acid as catalyst. Various novel (bridged) isoxazoline fused dihydrobenzofurans bearing two continuous quaternary stereocenters were achieved in moderate to good yields (up to 94%) with moderate to good enantioselectivities (up to 98% ee). The absolute configurations of two products were assigned by X-ray crystal structural analyses and a plausible reaction mechanism was proposed.

Graphical abstract: Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines

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Article information


Submitted
27 Aug 2020
Accepted
08 Oct 2020
First published
13 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines

H. Liu, Y. Yan, J. Zhang, M. Liu, S. Cheng, Z. Wang and X. Zhang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05807F

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