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Stereoselective syntheses of substituted succinic acid derivatives of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]

Davies, Stephen G.; Bashiardes, George; Bodwell, Graham J.; Collingwood, Stephen P.; Costello, James F.; Fletcher, Ai M.; Garner, Alan; Preston, Simon C.; Thomson, James E.

Authors

Stephen G. Davies

George Bashiardes

Graham J. Bodwell

Stephen P. Collingwood

Ai M. Fletcher

Alan Garner

Simon C. Preston

James E. Thomson



Abstract

© 2014 Elsevier Ltd. A range of alkyl- or aryl-substituted iron succinoyl complexes, incorporating the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)], were prepared in high regio- and diastereoselectivities by employing four successful strategies: (i) the alkylation of chiral enolate equivalents with tert-butyl bromoacetate; (ii) the mutual kinetic resolution of tert-butyl α-bromoacetate with a chiral acetate enolate equivalent; (iii) the alkylation of chiral succinoyl enolate equivalents; (iv) the conjugate addition of organolithium reagents or lithium amide reagents to chiral fumaroyl derivatives. Oxidative cleavage of the iron chiral auxiliary was shown to occur without compromising the stereochemical integrity of the succinoyl fragments.

Journal Article Type Article
Publication Date Nov 18, 2014
Journal Tetrahedron
Print ISSN 0040-4020
Electronic ISSN 1464-5416
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 70
Issue 46
Pages 8938-8951
APA6 Citation Davies, S. G., Bashiardes, G., Bodwell, G. J., Collingwood, S. P., Costello, J. F., Davies, S., …Thomson, J. E. (2014). Stereoselective syntheses of substituted succinic acid derivatives of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]. Tetrahedron, 70(46), 8938-8951. https://doi.org/10.1016/j.tet.2014.09.049
DOI https://doi.org/10.1016/j.tet.2014.09.049
Keywords stereoselective syntheses, succinic acid, iron chiral auxiliary
Publisher URL http://dx.doi.org/10.1016/j.tet.2014.09.049