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Issue 8, 2014
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Magnesium(II)-catalyzed asymmetric hetero-Diels–Alder reaction of Brassard's dienes with isatins

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Abstract

The first catalytic asymmetric hetero-Diels–Alder reaction of Brassard's dienes with isatins was realized using Mg(II)/N,N′-dioxide complexes as catalysts, affording the corresponding chiral spirolactones bearing tetrasubstituted centers in up to 99% yield with up to 99% ee and >99 : 1 dr within 3 hours. In the mechanism, based on the operando IR experiments, a predominant Diels–Alder pathway was found in the reaction. A possible transition state model was also proposed.

Graphical abstract: Magnesium(ii)-catalyzed asymmetric hetero-Diels–Alder reaction of Brassard's dienes with isatins

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Publication details

The article was received on 10 Oct 2013, accepted on 16 Nov 2013 and first published on 05 Dec 2013


Article type: Communication
DOI: 10.1039/C3CC47800A
Citation: Chem. Commun., 2014,50, 994-996
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    Magnesium(II)-catalyzed asymmetric hetero-Diels–Alder reaction of Brassard's dienes with isatins

    J. Zheng, L. Lin, Y. Kuang, J. Zhao, X. Liu and X. Feng, Chem. Commun., 2014, 50, 994
    DOI: 10.1039/C3CC47800A

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