Synthesis, resolution, and chiroptical properties of hemicryptophane cage controlling the chirality of propeller arrangement of a C
absolute configuration
chiral HPLC
chirality of triamide units
cyclotriveratrylene
enantiopure cages
Journal
Chirality
ISSN: 1520-636X
Titre abrégé: Chirality
Pays: United States
ID NLM: 8914261
Informations de publication
Date de publication:
Nov 2019
Nov 2019
Historique:
received:
10
04
2019
revised:
16
07
2019
accepted:
21
07
2019
pubmed:
3
9
2019
medline:
3
9
2019
entrez:
3
9
2019
Statut:
ppublish
Résumé
The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comparison of the experimental electronic circular dichroism (ECD) spectra with the calculated ones. X-ray molecular structures reveal that the capped benzene-1,3,5-tricarboxamide unit adopts a structurally chiral conformation in solid state: the chirality of CTV moiety controls the Λ or Δ orientation of the three amides.
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
910-916Informations de copyright
© 2019 Wiley Periodicals, Inc.
Références
Gabard J, Collet A. Synthesis of a (D3)-bis (cyclotriveratrylenyl) macrocage by stereospecific replication of a (C3)-subunit. J Chem Soc Chem Comm. 1981;1137-1139.
Brotin T, Dutasta JP. Cryptophanes and their complexes-present and future. Chem Rev. 2009;109:88-130.
Garel L, Dutasta JP, Collet A. Complexation of methane and chlorofluorocarbons by cryptophane-A in organic solution. Angew Chem Int Ed. 1993;22:169-1171.
Bartik K, Luhmer M, Dutasta JP, Collet AR, J. 129Xe and 1H NMR study of the reversible trapping of xenon by cryptophane-A in organic solution. J Am Chem Soc. 1998;120:784-791.
Fairchild RM, Holman KT. Selective anion encapsulation by a metalated cryptophane with a π-acidic interior. J Am Chem Soc. 2005;127:16364-16365.
Brotin T, Montserret R, Bouchet A, Cavagnat D, Linares M, Buffeteau T. High affinity of water-soluble cryptophanes for cesium cations. J Org Chem. 2012;77:1198-1201.
Garel L, Lozach B, Dutasta JP, Collet A. Remarkable effect of the receptor size in the binding of acetylcholine and related ammonium ions to water-soluble cryptophanes. J Am Chem Soc. 1993;115:11652-11653.
Canceill J, Lacombe L, Collet A. Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailormade cryptophane and determination of its maximum rotation. J Am Chem Soc. 1985;107:6993-6996.
Bouchet A, Brotin T, Linares M, Ågren H, Cavagnat D, Buffeteau T. Enantioselective complexation of chiral propylene oxide by an enantiopure water-soluble cryptophane. J Org Chem. 2011;76:4178-4181.
Canceill J, Collet A, Gabard J, Kotzyba-Hibert F, Speleands LJM. Macropolycyclic receptor cages based on binding and shaping sub-units. Synthesis and properties of macrocycle cyclotriveratrylene combinations. Helv Chim Acta. 1982;65:1894-1897.
Zhang D, Martinez A, Dutasta JP. Emergence of hemicryptophanes: from synthesis to applications for recognition, molecular machines, and supramolecular catalysis. Chem Rev. 2017;117:4900-4942.
Hardie MJ. Recent advances in the chemistry of cyclotriveratrylene. Chem Soc Rev. 2010;39:516-527.
Brotin T, Guy L, Martinez A, Dutasta JP. Enantiopur supramolecular cages: synthesis and chiral recognition Properties. Top Curr Chem. 2013;341:177-230.
Long A, Perraud O, Albalat M, Robert V, Dutasta JP, Martinez A. Helical chirality induces a substrate-selectivity switch in carbohydrates recognitions. J Org Chem. 2018;83:6301-6306.
Zhang D, Mulatier JC, Cochrane JR, et al. Helical, axial, and central chirality combined in a single cage: synthesis, absolute configuration, and recognition properties. Chem Eur J. 2016;22:8038-8042.
Perraud O, Robert V, Gornitzka H, Martinez A, Dutasta JP. Gathering cation-π and anion-π interactions for zwitterions recognition. Angew Chem Int Ed. 2012;51:504-508.
Schmitt A, Chatelet B, Collin S, Dutasta JP, Martinez A. Chiral discrimination of ammonium neurotransmitters by C3-symmetric enantiopure hemicryptophane hosts. Chirality. 2013;25:475-479.
Long A, Perraud O, Jeanneau E, Aronica C, Dutasta JP, Martinez A. A hemicryptophane with a triple-stranded helical structure. Beilstein J Org Chem. 2018;14:1885-1889.
Zimbron JM, Caumes X, Li Y, Thomas CM, Raynal M, Bouteiller L. Real-time control of the enantioselectivity of a supramolecular catalyst allows selecting the configuration of consecutively formed stereogenic centers. Angew Chem Int Ed. 2017;56:14016-14019.
Kulkarni C, Meijer EW, Palmans ARA. Cooperativity scale: a structure-mechanism correlation in the self-assembly of benzene-1,3,5-tricarboxamides. Acc Chem Res. 2017;50:1928-1936.
Das A, Vantomme G, Markvoort A, et al. Supramolecular copolymers: structure and composition revealed by theoretical modeling. J Am Chem Soc. 2017;139:7036-7044.
Garzoni M, Baker MB, Leenders CMA, et al. Effect of H-bonding on order amplification in the growth of a supramolecular polymer in water. J Am Chem Soc. 2016;138:13985-13995.
Desmarchelier A, Caumes X, Raynal M, Vidal-Ferran A, van Leeuwen PWNM, Bouteiller L. Correlation between the selectivity and the structure of an asymmetric catalyst built on a chirally amplified supramolecular helical scaffold. J Am Chem Soc. 2016;138:4908-4916.
Caumes X, Baldi A, Gontard G, et al. Bouteiller L Tuning the structure of 1,3,5-benzene tricarboxamide self-assemblies through stereochemistry. Chem Commun. 2016;52:13369-13372.
Desmarchelier A, Raynal M, Brocorens P, Vanthuyne N, Bouteiller L. Revisiting the assembly of amino ester-based benzene-1,3,5-tricarboxamides: chiral rods in solution. Chem Commun. 2015;51:7397-7400.
Gillissen MAJ, Koenigs MME, Spiering JJH, et al. Triple helix formation in amphiphilic discotics: demystifying solvent effects in supramolecular self-assembly. J Am Chem Soc. 2014;136:336-343.
Raynal M, Portier F, van Leeuwen PWNM, Bouteiller L. Tunable asymmetric catalysis through ligand stacking in chiral rigid rods. J Am Chem Soc. 2013;135:17687-17690.
Chatelet B, Payet E, Perraud O, et al. Shorter and modular synthesis of hemicryptophane-tren derivatives. Org Lett. 2011;13:3706-3709.
Lefevre S, Zhang D, Godart E, et al. Large-scale synthesis of enantiopure molecular cages: chiroptical and recognition properties. Chem Eur J. 2016;22:2068-2074.
Canceill J, Collet A, Gabard J, Gottarelli G, Spada GP. Exciton approach to the optical activity of C3-cyclotriveratrylene derivatives. J Am Chem Soc. 1985;107:1299-1308.
Chatelet B, Joucla L, Padula D, et al. Remote control of helical chirality: thermodynamic resolution of a racemic mixture of CTV units by remote stereogenic centers. Org Lett. 2015;17:500-503.
Long A, Colomban C, Jean M, et al. Enantiopure C1-cyclotriveratrylene with a reversed spatial arrangement of the substituents. Org. Lett. 2019;21:160-165.
Gosse I, Robeyns K, Bougault C, Martinez A, Tinant B, Dutasta JP. Synthesis and structural studies of gallium (III) and iron (III) hemicryptophane complexes. Inorg Chem. 2016;55:1011-1013.
Martinez A, Robert V, Gornitzka H, Dutasta JP. Controlling helical chirality in atrane structures: solvent dependent chirality sense in hemicryptophane oxidovanadium(V) complexes. Chem Eur J. 2010;16:520-527.
Martinez A, Guy L, Dutasta JP. Reversible, solvent-induced chirality switch in atrane structure: control of the unidirectional motion of the molecular propeller. J Am Chem Soc. 2010;132:16733-16734.