Stereochemical aspects of nucleophilic addition reactions to alkoxycarbene cations of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]

Stephen G. Davies; Ai M. Fletcher; Timothy R. Maberly; James E. Thomson

doi:10.1039/C3NJ00518F

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Stereochemical aspects of nucleophilic addition reactions to alkoxycarbene cations of the iron chiral auxiliary [(η⁵-C₅H₅)Fe(CO)(PPh₃)]†

Stephen G. Davies,*^a Ai M. Fletcher,^a Timothy R. Maberly^a and James E. Thomson^a

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^a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk
Fax: +44 (0)1865 275633
Tel: +44 (0)1865 275695

Abstract

Alkoxy carbene complexes incorporating the iron chiral auxiliary [(η⁵-C₅H₅)Fe(CO)(PPh₃)] were prepared in good yields from either the corresponding acyl complexes or methoxymethyl complex of the auxiliary. A range of nucleophilic addition reactions to these alkoxy carbene complexes showed moderate to high diastereoselectivities and the reactive conformations of the carbene complexes under these conditions are discussed.

This article is part of the themed collection: In honour of Bernard Meunier

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Article information

DOI: https://doi.org/10.1039/C3NJ00518F
Article type: Letter
Submitted: 15 May 2013
Accepted: 14 Jun 2013
First published: 17 Jun 2013

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New J. Chem., 2013,37, 3406-3410

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Stereochemical aspects of nucleophilic addition reactions to alkoxycarbene cations of the iron chiral auxiliary [(η⁵-C₅H₅)Fe(CO)(PPh₃)]

S. G. Davies, A. M. Fletcher, T. R. Maberly and J. E. Thomson, New J. Chem., 2013, 37, 3406 DOI: 10.1039/C3NJ00518F

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