Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 13, Pages 5102-5107Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913781
Keywords
asymmetric catalysis; DFT; mechanically interlocked molecules; rotaxanes; supramolecular chemistry
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Funding
- Fonds der Chemischen Industrie (Liebig Fellowship)
- German Research Foundation (DFG) [NI1273/2-1]
- German Science Foundation (DFG)
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Heterobifunctional rotaxanes serve as efficient catalysts for the addition of malonates to Michael acceptors. We report a series of four different heterobifunctional rotaxanes, featuring an amine-based thread and a chiral 1,1 '-binaphthyl-phosphoric-acid-based macrocycle. High-level DFT calculations provided mechanistic insights and enabled rational catalyst improvements, leading to interlocked catalysts that surpass their non-interlocked counterparts in terms of reaction rates and stereoselectivities.
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