Carbonylative C-C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides

Andrew G Dalling; Takayuki Yamauchi; Niall G McCreanor; Lydia Cox; John F Bower

doi:10.1002/anie.201811460

Carbonylative C-C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides

Angew Chem Int Ed Engl. 2019 Jan 2;58(1):221-225. doi: 10.1002/anie.201811460. Epub 2018 Nov 29.

Authors

Andrew G Dalling¹, Takayuki Yamauchi¹, Niall G McCreanor¹, Lydia Cox¹, John F Bower¹

Affiliation

¹ School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.

PMID: 30397992
DOI: 10.1002/anie.201811460

Abstract

Rh-catalyzed carbonylative C-C bond activation of cyclopropylamides generates configurationally stable rhodacyclopentanones that engage tethered alkenes in (3+1+2) cycloadditions. These studies provide the first examples of multicomponent cycloadditions that proceed through C-C bond activation of "simple" electron poor cyclopropanes.

Keywords: C−C activation; cycloaddition; cyclopropane; rhodium.

Publication types

Research Support, Non-U.S. Gov't

Abstract

Publication types

Grants and funding