Author
Listed:
- Depeng Zhao
(Centre for System Chemistry, Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen)
- Thomas M. Neubauer
(Centre for System Chemistry, Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen)
- Ben L. Feringa
(Centre for System Chemistry, Stratingh Institute for Chemistry, Faculty of Mathematics and Natural Sciences, University of Groningen)
Abstract
Chirality plays a fundamental role in biology and chemistry and the precise control of chirality in a catalytic conversion is a key to modern synthesis most prominently seen in the production of pharmaceuticals. In enantioselective metal-based catalysis, access to each product enantiomer is commonly achieved through ligand design with chiral bisphosphines being widely applied as privileged ligands. Switchable phosphine ligands, in which chirality is modulated through an external trigger signal, might offer attractive possibilities to change enantioselectivity in a catalytic process in a non-invasive manner avoiding renewed ligand synthesis. Here we demonstrate that a photoswitchable chiral bisphosphine based on a unidirectional light-driven molecular motor, can be used to invert the stereoselectivity of a palladium-catalysed asymmetric transformation. It is shown that light-induced changes in geometry and helicity of the switchable ligand enable excellent selectivity towards the racemic or individual enantiomers of the product in a Pd-catalysed desymmetrization reaction.
Suggested Citation
Depeng Zhao & Thomas M. Neubauer & Ben L. Feringa, 2015.
"Dynamic control of chirality in phosphine ligands for enantioselective catalysis,"
Nature Communications, Nature, vol. 6(1), pages 1-7, May.
Handle:
RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms7652
DOI: 10.1038/ncomms7652
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