Journal
CHEMICAL SCIENCE
Volume 2, Issue 12, Pages 2314-2320Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1sc00468a
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Funding
- Czech Science Foundation [203/09/1614, P207/10/2391, 203/08/1428, 203/09/P485]
- IOCB [Z40550506]
- MSMT [21/2011]
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A dicationic [6]helicene congener captured on the racemization pathway in its saddle-shaped geometry is introduced. Synthesis, structure, resolution, and dynamic properties of this chiral [6]saddlequat in-between and its highly stereocontrolled transformation into enantiopure [6]helquat are discussed and demonstrated. The dynamic aspects established by experiment and supported by detailed DFT-D calculations are presented visually in the form of a movie (electronic table-of-contents and electronic supplementary information). The title [6]saddlequat was found to be an isolable chiral species on the entirely chiral enantiomerization pathway of a [6]helquat that is discussed as an example of Mislow's rubber glove'' molecule.
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