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Issue 40, 2016
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The ligand influence in stereoselective carbene transfer reactions promoted by chiral metal porphyrin catalysts

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Abstract

The use of diazo reagents of the general formula N2C(R)(R1) as carbene sources to create new C–C bonds is of broad scientific interest due to the intrinsic sustainability of this class of reagents. In the presence of a suitable catalyst, diazo reagents react with several organic substrates with excellent stereo-control and form N2 as the only by-product. In the present report the catalytic efficiency of metal porphyrins in promoting carbene transfer reactions is reviewed with emphasis on the active role of the porphyrin skeleton in stereoselectively driving the carbene moiety to the target substrate. The catalytic performances of different metal porphyrins are discussed and have been related to the structural features of the ligand with the final aim of rationalizing the strict correlation between the three-dimensional structure of the porphyrin ligand and the stereoselectivity of carbene transfer reactions.

Graphical abstract: The ligand influence in stereoselective carbene transfer reactions promoted by chiral metal porphyrin catalysts

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Article information


Submitted
25 May 2016
Accepted
16 Jun 2016
First published
17 Jun 2016

This article is Open Access

Dalton Trans., 2016,45, 15746-15761
Article type
Perspective
Author version available

The ligand influence in stereoselective carbene transfer reactions promoted by chiral metal porphyrin catalysts

D. Intrieri, D. M. Carminati and E. Gallo, Dalton Trans., 2016, 45, 15746
DOI: 10.1039/C6DT02094A

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