Melchior Cini
Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance
Cini, Melchior; Bradshaw, Tracey D.; Woodward, Simon; Lewis, William
Authors
Tracey D. Bradshaw
SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry
William Lewis
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.
Citation
Cini, M., Bradshaw, T. D., Woodward, S., & Lewis, W. (2015). Asymmetric pentafulvene carbometalation-access to enantiopure titanocene dichlorides of biological relevance. Angewandte Chemie International Edition, 54(47), https://doi.org/10.1002/anie.201508034
Journal Article Type | Article |
---|---|
Acceptance Date | Aug 26, 2015 |
Online Publication Date | Oct 12, 2015 |
Publication Date | Nov 16, 2015 |
Deposit Date | Oct 14, 2016 |
Publicly Available Date | Oct 14, 2016 |
Journal | Angewandte Chemie International Edition |
Print ISSN | 1433-7851 |
Electronic ISSN | 1521-3773 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 54 |
Issue | 47 |
DOI | https://doi.org/10.1002/anie.201508034 |
Public URL | https://nottingham-repository.worktribe.com/output/766531 |
Publisher URL | http://onlinelibrary.wiley.com/doi/10.1002/anie.201508034/full |
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. |
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