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  Stereochemical Communication within a Chiral Ion Pair Catalyst

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.

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 Creators:
Merten, Christian1, Author
Pollok, Corina H.1, Author
Liao, Saihu2, Author              
List, Benjamin2, Author              
Affiliations:
1Fakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstrasse 150, 44801 Bochum (Germany), ou_persistent22              
2Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: asymmetric catalysis; asymmetric counterion-directed catalysis (ACDC); chirality transfer; ionic interactions; vibrational circular dichroism
 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.

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Language(s): eng - English
 Dates: 2015-02-092015-06-232015-07-20
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201501271
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 54 (30) Sequence Number: - Start / End Page: 8841 - 8845 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851