One-pot formation of fluorescent γ-lactams having an α-phosphorus ylide moiety through three-component α(δ')-Michael reactions of phosphines with an enyne and N-tosyl aldimines.
We demonstrate a straightforward synthesis of γ-lactams possessing an α-phosphorus ylide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial α(δ')-attack of phosphines to an enyne in up to 79% yield. The investigated multicomponent reaction tolerates a variety of triarylphosphines and electron-poor aldimines to give γ-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.
Department of Applied Chemistry, National Chiao Tung University, 1001 Ta Hsueh Road, Hsinchu, Taiwan 30010, Republic of China. jscchuang@faculty.nctu.edu.tw.
Yu-Wei
YW
Lin
Jie-Cheng
JC
Deng
You-Zung
YZ
Hsieh
Shih-Ching
SC
Chuang