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

Yu Wei Lin, Jie Cheng Deng, You-Zung Hsieh, Shih-Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

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. This journal is

Original languageEnglish
Pages (from-to)162-170
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number1
DOIs
StatePublished - 7 Jan 2014

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