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
Repository Citation
Molleti, N.,
Bjornberg, C.,
Kang, J. Y.
(2016).
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.
Organic and Biomolecular Chemistry, 14(45),
10695-10704.
http://dx.doi.org/10.1039/c6ob01987k