Gold-catalyzed N, O-functionalization of 1, 4-diyn-3-ols with N-hydroxyanilines to form highly functionalized pyrrole derivatives. Issue 17 (8th February 2018)

• Record Type: Journal Article
• Authors: Hsu, Yu-Chen; Hsieh, Shu-An; Li, Po-Hsuan; Liu, Rai-Shung
• Is Part Of: Chemical communications. Volume 54:Issue 17(2018)
• Page Start: 2114
• Page End: 2117
• Publication Date: 2018-02-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc00330k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : This work describes new N, O-functionalization of 1, 4-diyn-3-ols with N -hydroxyanilines to yield highly functionalized pyrrole derivatives. Abstract : This work describes new N, O-functionalization of 1, 4-diyn-3-ols with N -hydroxyanilines to yield highly functionalized pyrrole derivatives. In a postulated mechanism, N -hydroxyaniline attacks the more electron-rich alkynes via regioselective N-attack to form unstable ketone-derived nitrones that react with their tethered alkynes via an intramolecular oxygen-transfer to form α-oxo gold carbenes. This new method is applicable to a short synthesis of a bioactive molecule, a PDE4 inhibitor.