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1 article(s) from Krajnc, Matthias

BINOL as a chiral element in mechanically interlocked molecules

Matthias Krajnc and
Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

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Graphical Abstract

Figure 1: Molecular structures of (R)-BINOL (left) and (S)-BINOL (right).

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Figure 2: Synthesis of Sauvage´s [2]catenanes (S,S)-5 and (S,S)-6 containing two BINOL units by the passive m...

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Figure 3: Synthesis of Saito´s [2]rotaxane (R)-10 from a BINOL-based macrocycle by the active metal template ...

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Figure 4: Synthesis of Stoddart´s [2]rotaxane (rac)-14 by an ammonium crown ether template.

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Figure 5: Synthesis of Stoddart´s BINOL-containing [2]catenanes 18/20/22/24 by π–π recognition.

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Figure 6: Synthesis of Takata´s rotaxanes featuring chiral centers on the axle: a) rotaxane (R,R,R/S)-27 obta...

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Figure 7: Takata´s chiral polyacetylenes 32/33 featuring BINOL-based [2]rotaxane side chains.

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Figure 8: Synthesis of Takata´s chiral thiazolium [2]rotaxanes (R)-35a/b and (R)-38.

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Figure 9: Results for the asymmetric benzoin condensation of benzaldehyde (39) with catalysts (R)-35a/b and (R...

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Figure 10: Synthesis of Takata´s pyridine-based [2]rotaxane (R)-42.

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Figure 11: The asymmetric desymmetrization reaction of meso-1,2-diols with rotaxane (R)-42.

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Figure 12: Synthesis of Niemeyer´s axially chiral [2]catenane (S,S)-47.

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Figure 13: Results for the enantioselective transfer hydrogenation of 2-phenylquinoline with catalysts (S,S)-47...

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Figure 14: Synthesis of Niemeyer´s chiral [2]rotaxanes (S)-56/57.

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Figure 15: Results for the enantioselective Michael addition with different rotaxane catalysts (S)-56a/56b/57a/...

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Figure 16: Synthesis of Beer´s [2]rotaxanes 64a/b for anion recognition.

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Figure 17: Association constants of different anions (used as the Bu₄N⁺ salts) to the [2]rotaxanes (S)-64a/b a...

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Figure 18: Synthesis of Beer´s [3]rotaxane (S)-68.

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Figure 19: Association constants of different anions (used as the Bu₄N⁺-salts) to the [2]rotaxane (S)-68 and a...

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Review

Published 06 May 2022

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