Issue 18, 2015

Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(iii)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

Abstract

An asymmetric inverse-electron-demand hetero-Diels–Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N′-dioxide–Sc(III) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96% ee and >19 : 1 dr) under mild reaction conditions. A concerted reaction pathway was confirmed by Operando IR and control experiments.

Graphical abstract: Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(iii)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

Supplementary files

Article information

Article type
Communication
Submitted
27 Dec 2014
Accepted
27 Jan 2015
First published
04 Feb 2015

Chem. Commun., 2015,51, 3835-3837

Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

H. Hu, Y. Liu, J. Guo, L. Lin, Y. Xu, X. Liu and X. Feng, Chem. Commun., 2015, 51, 3835 DOI: 10.1039/C4CC10343B

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