Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 45, Pages 10695-10704Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6ob01987k
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- University of Nevada Las Vegas
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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.
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