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

Cini, Melchior; Bradshaw, Tracey D.; Woodward, Simon; Lewis, William

Authors

Melchior Cini

Tracey D. Bradshaw

Simon Woodward

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.

Journal Article Type Article
Publication Date Nov 16, 2015
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 54
Issue 47
APA6 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), doi:10.1002/anie.201508034
DOI https://doi.org/10.1002/anie.201508034
Publisher URL http://onlinelibrary.wiley.com/doi/10.1002/anie.201508034/full
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
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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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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