Issue 6, 2003
From the journal:

New Journal of Chemistry

l-Prolinoyl chiral picket iron porphyrins evaluated for the enantioselective epoxidation of alkenes

Bernard Boitrel*a  and  Valérie Baveux-Chambenoîtb  

* Corresponding authors

a Laboratoire Organométalliques et Catalyse: Chimie et Electrochimie Moléculaire (CNRS UMR 6509), Institut de Chimie de Rennes, Université de Rennes 1, Campus de Beaulieu, Rennes cedex, France
E-mail: Bernard.Boitrel@univ-rennes1.fr
Fax: +33 (0)2 23 23 56 37
Tel: +33 (0)2 23 23 63 72

b Laboratoire Synthèse et Electrosynthèse Organométalliques (FRE2595), Université de Bourgogne, 6, Bd Gabriel, Dijon, France

Abstract

Four atropisomers of an L-prolinoyl picket porphyrin were synthesised from tetra-o-aminophenyl porphyrin (TAPP) and were evaluated as alkene epoxidation catalysts after incorporation of iron in the porphyrin core. In the case of the αααα atropisomer bearing the four amino groups on the same side, a bulky base was employed in order to suppress the eventual reaction on the non-functionalised side of the porphyrin. The resulting enantioselectivities were compared with either other chiral motifs or with the corresponding strapped porphyrins. The enantioselectivities obtained with picket porphyrins are as high as those for strapped porphryins, and in some cases, even higher.

Graphical abstract: l-Prolinoyl chiral picket iron porphyrins evaluated for the enantioselective epoxidation of alkenes

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Article information

DOI
https://doi.org/10.1039/B212480G
Article type
Paper
Submitted
17 Dec 2002
Accepted
30 Jan 2003
First published
13 May 2003

New J. Chem., 2003,27, 942-947

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L-Prolinoyl chiral picket iron porphyrins evaluated for the enantioselective epoxidation of alkenes

B. Boitrel and V. Baveux-Chambenoît, New J. Chem., 2003, 27, 942 DOI: 10.1039/B212480G

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