Stephen G. Davies
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
George Bashiardes
Graham J. Bodwell
Stephen P. Collingwood
James Costello James.Costello@uwe.ac.uk
Senior Lecturer
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.
Citation
Davies, S. G., Bashiardes, G., Bodwell, G. J., Collingwood, S. P., Costello, J. F., Fletcher, A. M., …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
Journal Article Type | Article |
---|---|
Publication Date | Nov 18, 2014 |
Deposit Date | Oct 29, 2014 |
Publicly Available Date | Mar 28, 2024 |
Journal | Tetrahedron |
Print ISSN | 0040-4020 |
Electronic ISSN | 1464-5416 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 70 |
Issue | 46 |
Pages | 8938-8951 |
DOI | https://doi.org/10.1016/j.tet.2014.09.049 |
Keywords | stereoselective syntheses, succinic acid, iron chiral auxiliary |
Public URL | https://uwe-repository.worktribe.com/output/807642 |
Publisher URL | http://dx.doi.org/10.1016/j.tet.2014.09.049 |
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