Issue 44, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Sep 2017
Accepted
25 Oct 2017
First published
25 Oct 2017

Org. Biomol. Chem., 2017,15, 9465-9474

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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