Cs2CO3-mediated ring-opening reactions of nitrocyclopropanes via in situ generated allenes with phosphite triesters: stereoselective construction of (E)-vinylphosphonates

Abstract

Vinylphosphonate scaffolds are found frequently in diverse functional molecules. Herein, a novel reaction of phosphite triesters with nitrocyclopropanes via in situ generated key intermediate allenes was realized. By this strategy, vinylphosphonate derivatives were synthesized in moderate to excellent yields (up to 95% yield) with regio- and E-stereo-selectivities. Moreover, the reaction is operationally simple, mild, and transition metal-free, uses a simple inorganic base, and can be carried out on a gram scale.