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Heterobifunctional Rotaxanes for Asymmetric Catalysis.


ABSTRACT: 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.

SUBMITTER: Pairault N 

PROVIDER: S-EPMC7154720 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Heterobifunctional Rotaxanes for Asymmetric Catalysis.

Pairault Noël N   Zhu Hui H   Jansen Dennis D   Huber Alexander A   Daniliuc Constantin G CG   Grimme Stefan S   Niemeyer Jochen J  

Angewandte Chemie (International ed. in English) 20200116 13


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 stereoselectiv  ...[more]

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