α-Acylaminophosphonates possessing epoxyisoindolone moiety

α-Acylaminophosphonates possessing an epoxyisoindolone moiety were prepared with good stereoselectivity (de≥80%) by a tandem acylation/[4+2]-cycloaddition reaction between maleic anhydride and α-aminophosphonates derived from a furfurylamine. The cycloaddition products have an opposite orientation of epoxy and phosphonate groups, which was confirmed by NMR spectroscopy and X-ray crystal structure analysis.

Graphical abstractα-Acylaminophosphonates 6 possessing an epoxyisoindolone moiety were prepared with a good stereoselectivity (de≥80%) by a tandem acylation/[4+2]-cycloaddition reaction between maleic anhydride and α-aminophosphonates derived from a furfurylamine.Figure optionsDownload full-size imageDownload as PowerPoint slide