Shorter and Modular Synthesis of Hemicryptophane-tren Derivatives

Châtelet, Bastien; Payet, Elina; Perraud, Olivier; Dimitrov-Raytchev, Pascal; Chapellet, Laure-Lise; Dufaud, Véronique; Martinez, Alexandre; Dutasta, Jean‐Pierre

doi:10.1021/ol201355t

Cited by 41 publications

(68 citation statements)

References 28 publications

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“…[8][9][10] They were found to be a novel class of efficient supramolecular catalysts, 11,12 ion pair, 13 or zwitterions receptors 14,15 and led to the design of novel molecular mechanical components as propeller or gyroscope. Their syntheses mainly afford racemic mixtures, and their optical resolution is a common and challenging issue in the research of optically pure molecular hosts.…”

Section: Introductionmentioning

confidence: 99%

Absolute Configuration and Enantiodifferentiation of a Hemicryptophane Incorporating an Azaphosphatrane Moiety

et al. 2012

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The hemicryptophane racemate (±)-1 was optically resolved by semipreparative HPLC on Chiralpak IC column. The absolute configuration of each isolated enantiomer was established from the analysis of their electronic circular dichroism spectra. Enantiodifferentiation of the chiral cationic cage (±)-1 was evidenced in solution using Δ-TRISPHAT as chiral solvating agent, and the diastereomeric associations were observed in (1)H and (31)P NMR spectra.

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Section: Introductionmentioning

confidence: 99%

Absolute Configuration and Enantiodifferentiation of a Hemicryptophane Incorporating an Azaphosphatrane Moiety

et al. 2012

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“…31 Following this approach and using enantiopure tren derivatives should provide an easy way to obtain enantiopure hemicryptophanes. The reaction of the hemicryptophane precursor rac-2 bearing three aldehyde moieties with the enantiopure tren SSS-3a in a CHCl 3 /CH 3 OH mixture afforded the tris-imino-hemicryptophane 4a.…”

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confidence: 99%

Remote Control of Helical Chirality: Thermodynamic Resolution of a Racemic Mixture of CTV Units by Remote Stereogenic Centers

et al. 2015

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Enantiopure hemicryptophanes designed from the cyclotriveratrylene (CTV) unit display remarkable properties in selective host-guest recognition or as supramolecular catalysts. The unprecedented control of the helical chirality of the CTV unit by remote stereogenic centers of a tren moiety is reported, providing an original access to this highly promising class of host molecules. Although the chiral centers and the CTV unit are separated by more than 10 Å, one single diastereomer is formed; the nature of the diastereoselective process is discussed and the procedure is exemplified using different enantiopure tren derivatives. This work also highlights the influence of the chirality of the CTV unit on the whole cage structure.

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“…Compound 3 was prepared according to a previously reported two steps procedure: reaction between vanillic alcohol and dibromoethane affords compound 2 and the subsequent cyclization with scandium triflate in CH 3 CN gives CTV rac-3 in 18 % overall yield. 42 Mono-protection of the enantiopure S-binaphthol by an allyl group provides compound S-4, which then reacts with CTV rac-3 to give a mixture of the two diastereomers M-SSS-5…”

Section: Introductionmentioning

confidence: 99%

Cyclotriveratrylene-BINOL-Based Host Compounds: Synthesis, Absolute Configuration Assignment, and Recognition Properties

et al. 2016

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New host compounds combining a cyclotriveratrylene (CTV) unit and three binaphthol moieties have been synthesized enantiomerically and diastereomerically pure. The use of a chemical correlation allows for the assignment of their absolute configuration. The energy barrier of epimerization was measured, suggesting that no intramolecular hydrogen bonding occurs between the hydroxyl groups of the binaphthols. These open-shell host compounds were then tested in the recognition of carbohydrates; a preferential binding of mannose toward glucose was observed, and good diastereoselectivities were reached (up to 1:10). This recognition of sugar derivatives by open-shell CTV-based host compounds is unprecedented and opens up the way for a wider use of this easily accessible class of molecules as chiral sensors.

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Shorter and Modular Synthesis of Hemicryptophane-tren Derivatives

Cited by 41 publications

References 28 publications

Absolute Configuration and Enantiodifferentiation of a Hemicryptophane Incorporating an Azaphosphatrane Moiety

Absolute Configuration and Enantiodifferentiation of a Hemicryptophane Incorporating an Azaphosphatrane Moiety

Remote Control of Helical Chirality: Thermodynamic Resolution of a Racemic Mixture of CTV Units by Remote Stereogenic Centers

Cyclotriveratrylene-BINOL-Based Host Compounds: Synthesis, Absolute Configuration Assignment, and Recognition Properties

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