Croatica Chemica Acta, Vol. 91 No. 1, 2018.
Original scientific paper
https://doi.org/10.5562/cca3304
Synthesis of C2-Symmetric Bisphosphines and Their Application in Enantioselective Transition Metal Catalysis
Halil Zeki Gök
; Department of Biomedical Engineering, Faculty of Technology, Mehmet Akif Ersoy University, 15030, Bucak/Burdur, Turkey
Seda Kılıçarslan
; Department of Chemistry, Faculty of Arts and Sciences, Osmaniye Korkut Ata University, 80000, Osmaniye, Turkey
Yaşar Gök
; Department of Biomedical Engineering, Faculty of Technology, Mehmet Akif Ersoy University, 15030, Bucak/Burdur, Turkey
Abstract
C2-symmetric bisphosphine ligands (with a dioxolane backbone) have been synthesized by using corresponding chiral bromo-substituted hydrobenzoin derivatives in two steps with moderate yields. The last step for desired bisphosphines defined the electronic and steric properties of the chelating atoms by the treatment of aryl or alkyl substituted chlorophosphine compounds in the presence of a base. These synthesized ligands have been evaluated in different catalytic reactions. The first application has been the palladiumcatalyzed enantioselective allylic alkylation which is regarded as a remarkable reaction for forming enantioselective carbon-carbon bond (up to 63 % ee and 98 % chemical yield). The ruthenium-catalyzed enantioselective transfer hydrogenation reaction has been the second application for the evaluating of the catalysts (up to > 99 % conversion with no enantioselectivity).
This work is licensed under a Creative Commons Attribution 4.0 International License.
Keywords
synthesis; bisphosphine; catalysis; chirality; enantioselectivity
Hrčak ID:
199969
URI
Publication date:
2.1.2018.
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