Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Brønsted Acid
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- Raja Mitra
- Institute of Organic Chemistry Department of Chemistry University of Duisburg-Essen Universitätsstr. 7 45141 Essen Germany
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- Hui Zhu
- Mulliken Center for Theoretical Chemistry Rheinische Friedrich-Wilhelms-Universität Bonn Beringstr. 4 53115 Bonn Germany
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- Stefan Grimme
- Mulliken Center for Theoretical Chemistry Rheinische Friedrich-Wilhelms-Universität Bonn Beringstr. 4 53115 Bonn Germany
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- Jochen Niemeyer
- Institute of Organic Chemistry Department of Chemistry University of Duisburg-Essen Universitätsstr. 7 45141 Essen Germany
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説明
<jats:title>Abstract</jats:title><jats:p>Interlocked molecules, such as catenanes, rotaxanes, and molecular knots, have become interesting candidates for the development of sophisticated chemical catalysts. Herein, we report the first application of a catenane‐based catalyst in asymmetric organocatalysis, revealing that the catenated catalyst shows dramatically increased stereoselectivities (up to 98 % <jats:italic>ee</jats:italic>) in comparison to its non‐interlocked analogues. A mechanistic rationale for the observed differences was developed by DFT studies, suggesting that the involvement of two catalytically active groups in the stereodetermining reaction step is responsible for the superior selectivity of the interlocked catalyst.</jats:p>
収録刊行物
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 56 (38), 11456-11459, 2017-07-04
Wiley