Title

Phospha-Michael Addition Reaction of Maleimides Employing N-heterocyclic Phosphine-thiourea as a Phosphonylation Reagent: Synthesis of 1-aryl-2,5-dioxopyrrolidine-3-yl-phosphonate Derivatives

Document Type

Article

Publication Date

1-1-2016

Publication Title

Organic and Biomolecular Chemistry

Volume

14

Issue

45

First page number:

10695

Last page number:

10704

Abstract

N-Heterocyclic phosphine (NHP)-thiourea as a novel phosphonylation reagent has been successfully applied for the phospha-Michael reaction of maleimides under catalyst and additive free reaction conditions. This methodology enables desymmetrization of a variety of maleimide derivatives to provide 1-aryl-2,5-dioxopyrrolidine-3-yl-phosphonates in up to 92% yield. Synthetic manipulation of this Michael adduct afforded an ethylphosphonate and a phosphino lactam. Furthermore, a scale-up experiment for its practical usage as a versatile precursor in organic synthesis was readily demonstrated. © The Royal Society of Chemistry.

Language

English

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