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Journal Article

Stereochemical Communication within a Chiral Ion Pair Catalyst

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Liao,  Saihu
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Merten, C., Pollok, C. H., Liao, S., & List, B. (2015). Stereochemical Communication within a Chiral Ion Pair Catalyst. Angewandte Chemie International Edition, 54(30), 8841-8845. doi:10.1002/anie.201501271.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-1845-4
Abstract
Ionic interactions are increasingly appreciated as a key, asymmetry-inducing factor in enantioselective catalytic transformations, including those involving Brønsted acid or base catalysis, phase-transfer catalysis, and related processes. However, a detailed understanding of these interactions is often lacking. Herein, we show how an enantiopure anion enforces a chiral conformation onto a catalytically relevant achiral cation. Specifically, we use vibrational circular dichroism (VCD) spectroscopy to monitor the transmission of stereochemical information from a chiral phosphate anion to a flexible manganese(III)–salen cation. We show that VCD can be used to study solvent effects and that the obtained chiroptical data directly and quantitatively correlate with the experimentally observed enantioselectivity in an asymmetric olefin epoxidation reaction.