One-pot formation of fluorescent gamma-lactams having an alpha-phosphorus ylide moiety through three-component alpha(delta ')-Michael reactions of phosphines with an enyne and N-tosyl aldimines

Abstract

We demonstrate a straightforward synthesis of gamma-lactams possessing an a-phosphorus Aide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial alpha(delta')-attack of phosphines to an enyne in up to 79% yield. The investigated multicomponent reaction tolerates a variety of triaryl-phosphines and electron-poor aldimines to give gamma-lactams in one pot. One of the lactams, with the tri(p-tol)phosphine and 4-cyanophenyl moiety, exhibits fluorescence emission at 447 nm with a quantum yield of 0.11.