Correction: Substituent-controlled racemization of dissymmetric coordination capsules

Harada, Kentaro; Sekiya, Ryo; Maehara, Takeshi; Haino, Takeharu

doi:10.1039/c9ob90070e

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“…Diastereoenrichment (de %) was estimated by the integration of signals generated by G1 bound in the capsules (Table 1). Compared to that of 2Cu enriched by ( R )‐ G3 , the de % was improved from 55 de % to >95 de % [35] . In the case of 3Cu , the signal of G1 informed >95 de % (Figures S104 and S105 in the Supporting Information).…”

Section: Resultsmentioning

confidence: 96%

“…Compared to that of 2Cu enriched by (R)-G3, the de% was improved from 55 de % to >95 de %. [35] In the case of 3Cu, the signal of G1 informed >95 de % (Figures S104 and S105 in the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…[c] K inversion of THF + acetonitrile or chloroform + acetonitrile relative to that of THF or chloroform, respectively. [d] Very slow = negligible change in the CD intensity for 12 h. [e] Data from ref [35]…”

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confidence: 99%

“…The concentrations of 1Cu, 2Cu, and 3Cu were 1.0×10 À 2 mM throughout the measurements. In (c), the change in the CD intensity in THF is from ref [35]…”

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confidence: 99%

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Molecular Recognition Process in Resorcinarene‐based Coordination Capsules

Harada,

Sekiya,

Haino

2023

Chemistry A European J

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Cu and Ag capsules can take up various organic molecules. Their molecular recognition possibly involves partial dissociation and slippage. We investigated molecular recognition processes in Cu and Ag capsules by CD and 1H NMR spectroscopy and employed 4,4’‐diacetoxy biphenyl carrying two benzothiadiazole groups as a probe. CD and 1H NMR measurements reveal that the host‐guest complexation proceeds under second‐order reactions and that these capsules undergo partial dissociation to take up the probe in [D1]chloroform and [D8]THF. Slippage also contributes to host‐guest complexation for a Cu capsule that carries p‐methoxyphenyl groups on the 2,2’‐bipyridiyl arms. DFT calculations suggest that π/π stacking interactions between the electron‐rich p‐methoxyphenyl group and the electron‐poor 2,2’‐bipyridyl arm elongate the capsule, allowing the guest to access the cavity without partial dissociation.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

“…The concentrations of 1Cu, 2Cu, and 3Cu were 1.0×10 À 2 mM throughout the measurements. In (c), the change in the CD intensity in THF is from ref [35]…”

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confidence: 99%

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Molecular Recognition Process in Resorcinarene‐based Coordination Capsules

Harada,

Sekiya,

Haino

2023

Chemistry A European J

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Kinetic Resolution of Secondary Alcohols Catalyzed at the Exterior of Chiral Coordinated Capsules

Harada,

Sekiya,

Haino

2024

Chemistry A European J

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Confined spaces inside molecular hosts can function as reaction vessels. However, this concept significantly limits the scope of reactants. When the exterior of molecular hosts is used instead, we can ease the restriction because reactants are not necessary to be trapped inside molecular hosts, although studies along this line have not been reported. As a proof‐of‐concept of enantioselective reactions at the exterior of chiral molecular hosts, we utilized host‒guest complexes of enantiomerically enriched Cu‐coordinated capsules and guests possessing a catalytic center to realize the kinetic resolution of secondary alcohols. Under suitable reaction conditions, a selectivity factor of 2.6 was realized, demonstrating that the reactions occur at the exterior of the capsules. A series of experiments indicated that the substituents on the 2,2’‐bipyridyl arms and the alkyl chains on the lower rim contributed to the enantioselectivity of the reactions.

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Correction: Substituent-controlled racemization of dissymmetric coordination capsules

Abstract: Correction for ‘Substituent-controlled racemization of dissymmetric coordination capsules’ by Kentaro Harada et al., Org. Biomol. Chem., 2019, DOI: 10.1039/c9ob00388f.

Cited by 2 publications

References 0 publications

Molecular Recognition Process in Resorcinarene‐based Coordination Capsules

Molecular Recognition Process in Resorcinarene‐based Coordination Capsules

Kinetic Resolution of Secondary Alcohols Catalyzed at the Exterior of Chiral Coordinated Capsules

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