Issue 1, 2014

A non-diazo strategy to cyclopropanation via oxidatively generated gold carbene: The benefit of a conformationally rigid P,N-bidentate ligand

Abstract

What a trade: diazo ketones for alkynes? By utilizing a conformationally rigid P,N-bidentate ligand, highly efficient intramolecular cyclopropanation reactions using flexible and electronically neutral terminal alkyne substrates are realized via a sterically shielded tri-coordinated gold carbene intermediate. Bicyclic/tricyclic functionalized cyclopropyl ketones are formed in mostly good yields in three steps from readily available enones/enals, which compares favorably with related strategies based on the diazo approach in terms of step economy and operational safety. With this chemistry, we have expanded alkynes as surrogates of α-diazo ketones to cyclopropanation reactions.

Graphical abstract: A non-diazo strategy to cyclopropanation via oxidatively generated gold carbene: The benefit of a conformationally rigid P,N-bidentate ligand

Supplementary files

Article information

Article type
Research Article
Submitted
24 Dec 2013
Accepted
06 Jan 2014
First published
13 Feb 2014

Org. Chem. Front., 2014,1, 34-38

Author version available

A non-diazo strategy to cyclopropanation via oxidatively generated gold carbene: The benefit of a conformationally rigid P,N-bidentate ligand

K. Ji and L. Zhang, Org. Chem. Front., 2014, 1, 34 DOI: 10.1039/C3QO00080J

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