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.

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
• Deposit Date: Oct 29, 2014
• 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
• Contract Date: Jun 6, 2016