Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance

Cini, Melchior and Bradshaw, Tracey D. and Woodward, Simon and Lewis, William (2015) Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance. Angewandte Chemie International Edition, 54 (47). pp. 14179-14182. ISSN 1521-3773

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Abstract

Unprecedented asymmetric copper-catalyzed addition of ZnEt2 (ZnBu2) to the exocyclic C[DOUBLE BOND]C bond of pentafulvenes C5H4([DOUBLE BOND]CHAr) (Ar=2-MeOPh and related species) results in enantiomerically enriched (up to 93:7 e.r.) cyclopentadienyl ligands (C5H4CHEtAr; abbreviated CpR). Copper catalyst promotion with both chiral phosphoramidite ligands and a phosphate additive is vital in realizing both acceptable enantioselectivities and reaction rates. Enantiomeric CpR2TiCl2 complexes have been prepared; the (S,S) isomer is twice as active towards pancreatic, breast, and colon cancer cell lines as its (R,R) enantiomer at 24 h.

Item Type: Article
Additional Information: This is the peer reviewed version of the following article: Cini, M., Bradshaw, T. D., Woodward, S. and Lewis, W. (2015), Asymmetric Pentafulvene Carbometalation—Access to Enantiopure Titanocene Dichlorides of Biological Relevance. Angew. Chem. Int. Ed., 54: 14179–14182, which has been published in final form at http://dx.doi.org/10.1002/anie.201508034. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Schools/Departments: University of Nottingham UK Campus > Faculty of Science > School of Chemistry
University of Nottingham UK Campus > Faculty of Science > School of Pharmacy
Identification Number: https://doi.org/10.1002/anie.201508034
Depositing User: Eprints, Support
Date Deposited: 14 Oct 2016 08:28
Last Modified: 14 Oct 2016 11:11
URI: http://eprints.nottingham.ac.uk/id/eprint/37572

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