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Issue 44, 2017
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Azetidine-derived dinuclear zinc catalyzed asymmetric phospha-Michael addition of dialkyl phosphite to α,β-unsaturated carbonyl compounds

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Abstract

The asymmetric phospha-Michael addition of dialkyl phosphite to α,β-unsaturated carbonyl compounds by using an azetidine-derived dinuclear zinc catalyst was described. The catalyst was proved to be general and efficient for a broad spectrum of enones and α,β-unsaturated N-acylpyrroles. A series of phosphonate-containing compounds were generated with excellent enantioselectivities (up to 99% ee) and chemical yields (up to 99%) under mild conditions without using additives. The products were obtained with more than 95% ee for 23 examples of α,β-unsaturated carbonyl compounds. A positive nonlinear effect was observed and the possible mechanism was proposed.

Graphical abstract: Azetidine-derived dinuclear zinc catalyzed asymmetric phospha-Michael addition of dialkyl phosphite to α,β-unsaturated carbonyl compounds

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Publication details

The article was received on 04 Sep 2017, accepted on 25 Oct 2017 and first published on 25 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02222K
Citation: Org. Biomol. Chem., 2017,15, 9465-9474
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    Azetidine-derived dinuclear zinc catalyzed asymmetric phospha-Michael addition of dialkyl phosphite to α,β-unsaturated carbonyl compounds

    S. Liu, N. Shao, F. Li, X. Yang and M. Wang, Org. Biomol. Chem., 2017, 15, 9465
    DOI: 10.1039/C7OB02222K

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