Issue 12, 2022

ZnCl2-mediated stereo- and chemoselective synthesis of vinylphosphonates

Abstract

A highly chemo- and stereoselective synthesis of diethyl (E)-2-(alkylidene)-2-phosphonoacetonitriles via the Knoevenagel condensation reaction of carbonyl compounds with diethyl cyanomethylphosphonate in the presence of zinc chloride has been achieved. By the presented method, various E-isomers of arylmethylidene phosphonates rather than Horner–Wadsworth–Emmons olefination products were obtained in good to excellent yields. Their E configurations were determined by X-ray diffraction and NMR analyses. In addition, DFT calculations provided insights into the chemo- and stereoselectivity of the reaction.

Graphical abstract: ZnCl2-mediated stereo- and chemoselective synthesis of vinylphosphonates

Supplementary files

Article information

Article type
Paper
Submitted
06 Jan 2022
Accepted
25 Feb 2022
First published
03 Mar 2022

Org. Biomol. Chem., 2022,20, 2500-2507

ZnCl2-mediated stereo- and chemoselective synthesis of vinylphosphonates

B. Kaboudin, A. Moradi, H. Esfandiari, P. Daliri, F. Kazemi, H. Yanai and H. Aoyama, Org. Biomol. Chem., 2022, 20, 2500 DOI: 10.1039/D2OB00037G

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