Inherently chiral calixarenes: Synthesis, optical resolution, chiral recognition and asymmetric catalysis

International Journal of Molecular Sciences

Volumn 12, Issue 1, 2011, Pages 429-455

  Li, Shao Yong ^b   Xu, Yao Wei ^a   Liu, Jun Min ^a   Su, Cheng Yong ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b TIANJIN MEDICAL UNIVERSITY   (China)

Author keywords

Asymmetric catalysis; Chiral recognition; Inherently chiral calixarene; Optical resolution; Synthesis

Indexed keywords

CALIXARENE; PHENOL;

ACYLATION; ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHIRALITY; COLUMN CHROMATOGRAPHY; CONFORMATIONAL TRANSITION; CRYSTALLIZATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; FRAGMENTATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR RECOGNITION; OPTICAL RESOLUTION; SEPARATION TECHNIQUE; STEREOCHEMISTRY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CALIXARENES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79251630104     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12010429     Document Type: Article

References (73)

1. Gutsche, D.C. Calixarenes: An Introduction; Royal Society of Chemistry: Cambridge, UK, 2008; pp. 209-237.
2. Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M. Colorimetric Chiral Recogniton by a molecular Sensor. Nature 1996, 382, 522-524.
3. Pinkhassik, E.; Stibor, I.; Casnati, A.; Ungaro, R. Synthesis of Upper and Lower Rim Binaphthyl Bridged Calix[4]arenes: New Potential Chiral Hosts for Molecular Recognition and Catalysis. J. Org. Chem. 1997, 62, 8654-8659.
4. Castellano, R.K.; Nuckolls, C.; Rebek, J., Jr. Transfer of Chiral Information through Molecular Assembly. J. Am. Chem. Soc. 1999, 121, 11156-11163.
5. Prins, L.J.; Jong, F.D.; Timmerman, P.; Reinhoudt, D.N. An Enantiomerically Pure Hydrogen-bonded Assembly. Nature 2000, 408, 181-184.
6. Zheng, Y.-S.; Zhang, C. Exceptional Chiral Recognition of Racemic Carboxylic Acids by Calix[4]arenes Bearing Optically Pure α,β-Amino Alcohol Groups. Org. Lett. 2004, 6, 1189-1192.
7. Cherenok, S.; Vovk, A.; Muravyova, I.; Shivanyuk, A.; Kukhar, V.; Lipkowski, J.; Kalchenko, V. Calix[4]arene α-Aminophosphonic Acids: Asymmetric Synthesis and Enantioselective Inhibition of an Alkaline Phosphatase. Org. Lett. 2006, 8, 549-552.
8. Bonini, C.; Chiummiento, L.; Funicello, M.; Teresa Lopardo, M.; Lupattelli, P.; Laurita, A.; Cornia, A. Novel Chiral Calix[4]arenes by Direct Asymmetric Epoxidation Reaction. J. Org. Chem. 2008, 73, 4233-4236.
9. Gaeta, C.; de Rosa, M.; Fruilo, M.; Soriente, A.; Neri, P. Synthesis of Calix[4]arene Derivatives Bearing Chiral Pendant Groups as Ligands for Enantioselective Catalysis. Tetrahedron: Asymmetry 2005, 16, 2333-2340.
10. Quintard, A.; Darbost, U.; Vocanson, F.; Pellet-Rostaing, S.; Lemaire, M. Synthesis of New Calix[4]arene Based Chiral Ligands Bearing β-Amino Alcohol Groups and Their Application in Asymmetric Transfer Hydrogenation. Tetrahedron: Asymmetry 2007, 18, 1926-1933.
11. Marson, A.; Freixa, Z.; Kamer, P.C.J.; van Leeuwen, P.W.N.M. Chiral Calix[4]arene-Based Diphosphites as Ligands in the Asymmetric Hydrogenation of Prochiral Olefins. Eur. J. Inorg. Chem. 2007, 4587-4591.
12. Böhmer, V.; Kraft, D.; Tabatabai, M. Inherently Chiral Calixarenes. J. Incl. Phenom. Macro. Chem. 1994, 19, 17-39.
13. Cort, A.D.; Mandolini, L.; Pasquini, C.; Schiaffino, L. "Inherent chirality" and curvature. New J. Chem. 2004, 28, 1198-1199.
14. Szumna, A. Inherently Chiral Concave Molecules-from Synthesis to Applications. Chem. Soc. Rev. 2010, 39, 4274-4285.
15. No, K.H.; Gutsche, C.D. Calixarenes. 8. Short, Stepwise Synthesis of p-Phenylcalix[4]arene, p-Penyl-p-tert-butylcalix[4]arene, and Derived Products. J. Org. Chem. 1982, 47, 2713-2719.
16. Luo, J.; Zheng, Q.; Chen, C.; Huang, Z. Progress in Inherently Chiral Calixarenes. Prog. Chem. 2006, 18, 897-906.
17. McIldowie, M.J.; Mocerino, M.; Ogden, M.I. A Brief Review of Cn-Symmetric Calixarenes and Resorcinarenes. Supramol. Chem. 2010, 22, 13-39.
18. Böhmer, V.; Merkel, L.; Kunz, U. Asymmetrically-Substituted Calix[4]arenes. J. Chem. Soc., Chem. Commun. 1987, 896-897.
19. Casabianca, H.; Royer, J.; Satrallah, A.; Taty-C,A.; Vicens, J. Synthesis of Calix[4]arenas Presenting No Plane of Symmetry. Tetrahedron Lett. 1987, 28, 6595-6596.
20. Andreetti, G.D.; Böhmer, V.; Jordon, J.G.; Tabatabai, M.; Ugozzoli, F.; Vogt, W.; Wolfft, A. Dissymmetric Calix[4]arenes with C4- and C2-Symmetry. Synthesis, X-ray Structures, Conformational Fixation, and lH NMR Spectroscopic Studies. J. Org. Chem. 1993, 58, 4023-4032.
21. Iwamoto, K.; Shimizu, H.; Araki, K.; Shinkai, S. Syntheses and Optical Resolution of Calix[4]arenes with Molecular Asymmetry. Systematic Classification of All Possible Chiral Isomers Derivable from Calix[4]arene. J. Am. Chem. Soc. 1993, 115, 3997-4006.
22. Narumi, F.; Yamabuki, W.; Hattori, T.; Kameyama, H.; Miyano, S. Synthesis and Optical Resolution of an anti-O,O'-Dialkylated Calix[4]arene. Chem. Lett. 2003, 32, 320-321.
23. Pappalardo, S.; Caccamese, S.; Giunta, L. Stereoselective Synthesis and Optical Resolution of Chiral Calix[4]arenes with Mixed Ligating Functionalities. Tetrahedron Lett. 1991, 32, 7747-7750.
24. Böhmer, V.; Wolff, A.; Vogt, W. A New Route to Chiral Calix[4]arenes via 1,3-Derivatization. J. Chem. Soc., Chem. Commun. 1990, 14, 968-970.
25. Vysotsky, M.O.; Tairov, M.O.; Pirozhenko, V.V.; Kalchenko, V.I. Inherently Chiral Calix[4]arenes with Asymmetrical Superposition of Substituents at the Lower and the Upper Rims of Macrocycle. Tetrahedron Lett. 1998, 39, 6057-6060.
26. Li, S.Y.; Sun, B.; Xiao, Z.C.; Huang, M.H.; Xie, W.X.; Liu, J.M. One-Step Synthesis of Inherently Chiral p-tert-Butylcalix[4]azacrown. Chin. Chem. Lett. 2009, 20, 640-642.
27. Iwamoto, K.; Yanagi, A.; Arimura, T.; Matsuda, T.; Shinkai, S. Synthesis and Optical Resolution of a Chiral Calix[4]arene Asymmetrically-Substituted on the Lower Rim. Chem. Lett. 1990, 19, 1901-1904.
28. Browne, J.K.; McKervey, M.A.; Pitarch, M.; Russell, J.A. Enzymatic Synthesis of Nonracemic Inherently Chiral Calix[4]arenes by Lipase-Catalysed Transesterification. Tetrahedron Lett. 1998, 39, 1787-1790.
29. Bitter, I.; Grün, A.; Tóth, G.; Balázs, B.; Horváth, G.; Tóke, L. Studies on Calix(aza)crowms, II.1 Synthesis of Novel Proximal Doubly Bridged Calix[4]arenes by Intramolecular Ring Closure of syn-l,3- and 1,2-ω-Chloroalkylamides. Tetrahedron 1998, 54, 3857-3870.
30. Shu, C.-M.; Chung, W.-S. Synthesis of Calix[4]arenes with Four Different "Lower Rim" Substituents. J. Org. Chem. 1999, 64, 2673-2679.
31. Arnecke, R.; Böhmer, V.; Fergwon, G.; Pappalardo, S. Inherently Chiral Derivatives of Calix[5]crowns. Tetrahedron Lett. 1996, 37, 1497-1500.
32. No, K.; Kwon, K.M.; Kim, B.H. Asymmetrically Substituted Calix[5]arene Derivatives. Bull. Korean Chem. Soc. 1998, 19, 1395-1398.
33. Neri, P.; Rocco, C.; Consoli, G.M.L.; Piattelli, M. Conformational Isomerism of Calix[6]arenes: Isolation of Two Conformational Isomers of the 1,2-Bis(p-tert-butylbenzyl) Ether of p-tert- Butylcalix[6]arene. J. Org. Chem. 1993, 58, 6535-6537.
34. Janssen, R.G.; Verboom, W.; van Duynhoven, J.P.M.; van Velzen, E.J.J.; Reinhoudt, D.N. Cryptocalix[6]arenes; Molecules with a Larger Cavity. Tetrahedron Lett. 1994, 35, 6555-6558.
35. Kanamathareddy, S.; Gutsche, C.D. Synthesis and Conformational Properties of Calix[6]arenas Bridged on the Lower Rim: Self-Anchored Rotaxanes. J. Am. Chem. Soc. 1993, 115, 6572-6579.
36. Corrada Geraci, C.; Piattelli, M.; Neri, P. Inherent Chirality in Calix[8]arenes Exploiting the Steric Constraint of Two Intercrossing Polyether Chains. Tetrahedron Lett. 1996, 37, 7627-7630.
37. Hesek, D.; Inoue, Y.; Drew, M.G.B.; Beer, P.D.; Hembury, G.A.; Ishida, H.; Aoki, F. Acid-Promoted Rearrangement of Carbonate Functionality Anchored to the Lower Rim of a Calix[4]arene Skeleton: A New Class of Chiral Calix[4]arene and Its Chiroptical Properties. Org. Lett. 2000, 2, 2237-2240.
38. Sharma, S.K.; Gutsche, C.D. Synthesis and Reactions of Calix[4]arene Bisanhydrides. J. Org. Chem. 1999, 64, 3507-3512.
39. Ikeda, A.; Yoshimura, M.; Lhotak, P.; Shinkai, S. Synthesis and Optical Resolution of Naphthalene-Containing Inherently Chiral Calix[4]arenes Derived by Intramolecular Ring Closure or Stapling of Proximal Phenyl Units. J. Chem. Soc., Perkin Trans. 1996, 1945-1950.
40. Shirakawa, S.; Moriyama, A.; Shimizu, S. Design of a Novel Inherently Chiral Calix[4]arene for Chiral Molecular Recognition. Org. Lett. 2007, 9, 3117-3119.
41. Shimizu, S.; Moriyama, A.; Kito, K.; Sasaki, Y. Selective Synthesis and Isolation of All Possible Conformational Isomers of Proximally para-Disubstituted Calix[4]arene. J. Org. Chem. 2003, 68, 2187-2194.
42. Colasson, B.; Reinaud, O. Selective Hetero-Trisfunctionalization of the Large Rim of a Biomimetic Calix[6]arene Using Host-Guest Chemistry as a Synthetic Tool. J. Am. Chem. Soc. 2008, 130, 15226-15227.
43. Liu, J.-M.; Shi, J.-Y.; Xu, Y.-W.; Su, C.-Y.; Li, S.-Y. Synthesis of Inherently Chiral Wide Rim ABC-Substituted Calix[6]arene Derivatives. Supramol. Chem. 2010, doi:10.1080/10610278.2010.544733.
44. Reddy, P.A.; Gutache, C.D. Calixarenes. 32. Reactions of Calix[4]quinines. J. Org. Chem. 1993, 58, 3245-3251.
45. Verboom, W.; Bodewes, P.J.; van Essen, G.; Timmerman, P.; van Hummel, G.J.; Harkema, S.; Reinhoudt, D.N. A Novel Approach to Inherently Chiral Calix[4]arenes by Direct Introduction of a Substituent at the meta Position. Tetrahedron 1995, 51, 499-512.
46. Troisi, F.; Pierro, T.; Gaeta, C.; Carratù, M.; Neri, P. Appending Aromatic Moieties at the para- and meta-Position of Calixarene Phenol Rings via p-Bromodienone Route. Tetrahedron Lett. 2009, 50, 4416-4419.
47. Herbert, S.A.; Arnott, G.E. An Asymmetric Ortholithiation Approach to Inherently Chiral Calix[4]arenes. Org. Lett. 2009, 11, 4986-4989.
48. Xu, Z.-X.; Zhang, C.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. A New Approach to Enantiopure Inherently Chiral Calix[4]arenes: Determination of Their Absolute Configurations. Org. Lett. 2007, 9, 4447-4450.
49. Mastalerz, M.; Hüggenberg, W.; Dyker, G. Photochemistry of Styrylcalix[4]arenes. Eur. J. Org. Chem. 2006, 3977-3987.
50. Miao, R.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Efficient Syntheses and Resolutions of Inherently Chiral Calix[4]quinolines in the Cone and Partial-Cone Conformation. J. Org. Chem. 2005, 70, 7662-7671.
51. Shinkai, S.; Arimura, T.; Kawabata, H.; Murakami, H.; Araki, K.; Iwamoto, K.; Matsuda, T. Synthesis and Optical Resolution of an Asymmetrically Substituted Calix[4]arene. J. Chem. Soc., Chem. Commun. 1990, 1734-1736.
52. Caccamese, S.; Notti, A.; Pappalardo, S.; Parisi, M.F.; Principato, G. Inherently Chiral α-Picolyloxy-p-tert-Butylcalix[5]arene Crown Ethers: Synthesis, Structure Proof, and Enantioselective HPLC Resolution. Tetrahedron 1999, 55, 5505-5514.
53. Otsuka, H.; Shinkai, S. Definitive Evidence for Inhibition of Calix[6]arene Ring Inversion Obtained from a 1,3-Xylenyl-Bridged Chiral Calix[6]arene. J. Am. Chem. Soc. 1996, 118, 4271-4275.
54. Caccamese, S.; Principato, G.; Geraci, C.; Neri, P. Resolution of Inherently Chiral 1,4-2,5- Calix[8]bis-Crown-4 Derivatives by Enantioselective HPLC. Tetrahedron: Asymmetry 1997, 8, 1169-1173.
55. Cao, Y.-D.; Luo, J.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Preparation of Both Antipodes of Enantiopure Inherently Chiral Calix[4]crowns. J. Org. Chem. 2004, 69, 206-208.
56. Luo, J.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Synthesis and Optical Resolution of a Series of Inherently Chiral Calix[4]crowns with Cone and Partial Cone Conformations. Chem. Eur. J. 2005, 11, 5917-5928.
57. Xu, B.; Carroll, P.J.; Swager, T.M. Chiral Metallocalix[4]arenes: Resolution by Diastereomeric Tungsten(VI) Alkoxides. Angew. Chem. Int. Ed. Engl. 1996, 35, 2094-2097.
58. Li, S.-Y.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Preparation of Enantiopure Inherently Chiral Calix[5]arenes. Tetrahedron: Asymmetry 2005, 16, 641-645.
59. Boyko, V.I.; Shivanyuk, A.; Pyrozhenko, V.V.; Zubatyuk, R.I.; Shishkinb, O.V.; Kalchenkoa, V.I. A Stereoselective Synthesis of Asymmetrically Substituted Calix[4]arenecarbamates. Tetrahedron Lett. 2006, 47, 7775-7778.
60. Yakovenko, A.V.; Boyko, V.I.; Danylyuk, O.; Suwinska, K.; Lipkowski, J.; Kalchenko, V.I. Diastereoselective Lower Rim (1S)-Camphorsulfonylation as the Shortest Way to the Inherently Chiral Calix[4]arene. Org. Lett. 2007, 9, 1183-1185.
61. Xu, Z.-X.; Zhang, C.; Yang, Y.; Chen, C.-F.; Huang, Z.-T. Effective Nonenzymatic Kinetic Resolution of Racemic m-Nitro-Substituted Inherently Chiral Aminocalix[4]arenes. Org. Lett. 2008, 10, 477-479.
62. Xu, Z.-X.; Zhang, C.; Huang, Z.-T.; Chen, C.-F. Efficient Synthesis and Resolution of meta-Substituted Inherently Chiral Aminocalix[4]arene Derivatives. Chin. Sci. Bull. 2010, 55, 2859-2869.
63. Jin, T.; Monde, K. Synthesis and Optical Resolution of a Fluorescent Chiral Calix[4]arene with Two Pyrene Moieties Forming an Intramolecular Excimer. Chem. Commun. 1998, 1357-1358.
64. Luo, J.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Facile Synthesis and Optical Resolution of Inherently Chiral Fluorescent Calix[4]crowns: Enantioselective Recognition towards Chiral Leucinol. Tetrahedron 2005, 61, 8517-8528.
65. Shirakawa, S.; Moriyama, A.; Shimizu, S. Synthesis, Optical Resolution and Enantiomeric Recognition Ability of Novel, Inherently Chiral Calix[4]arenes: Trial Application to Asymmetric Reactions as Organocatalysts. Eur. J. Org. Chem. 2008, 5957-5964.
66. Kliachyna, M.A.; Yesypenko, O.A.; Pirozhenko, V.V.; Shishkina, S.V.; Shishkin, O.V.; Boyko, V.I.; Kalchenko, V.I. Synthesis, Optical Resolution and Absolute Configuration of Inherently Chiral Calixarene Carboxylic Acids. Tetrahedron 2009, 65, 7085-7091.
67. Dieleman, C.; Steyer, S.; Jeunesse, C.; Matt, D. Diphosphines Based on an Inherently Chiral Calix[4]arene Scaffold: Synthesis and Use in Enantioselective Catalysis. J. Chem. Soc., Dalton Trans. 2001, 2508-2517.
68. Xu, Z.-X.; Huang, Z.-T.; Chen, C-F. Synthesis and Structures of Novel Enantiopure Inherently Chiral Calix[4]arene-Derived Salphen Ligands and their Transition-Metal Complexes. Tetrahedron Lett. 2009, 50, 5430-5433.
69. Xu, Z.-X.; Li, G.-K.; Chen, C.-F.; Huang, Z.-T. Inherently Chiral Calix[4]arene-Based Bifunctional Organocatalysts for Enantioselective Aldol Reactions. Tetrahedron 2008, 64, 8668-8675.
70. Miao, R.; Xu, Z.-X.; Huang, Z.-T.; Chen, C.-F. Enantiopure Inherently Chiral Calix[4]arene Derivatives Containing Quinolin-2-yl-methanol moiety: Synthesis and Application in the Catalytic Asymmetric Addition of Diethylzinc to Benzaldehyde. Sci. China Ser. B Chem. 2009, 52, 505-512.
71. Shirakawa, S.; Kimura, T.; Murata, S.; Shimizu, S. Synthesis and Resolution of a Multifunctional Inherently Chiral Calix[4]arene with an ABCD Substitution Pattern at the Wide Rim: The Effect of a Multifunctional Structure in the Organocatalyst on Enantioselectivity in Asymmetric Reactions. J. Org. Chem. 2009, 74, 1288-1296.
72. Shirakawa, S.; Shimizu, S. Synthesis of an Inherently Chiral Calix[4]arene Amino Acid and its Derivatives: Their Application to Asymmetric Reactions as Organocatalysts. Eur. J. Org. Chem. 2009, 12, 1916-1924.
73. Shirakawa, S.; Shimizu, S. Improved Design of Inherently Chiral Calix[4]arenes as Organocatalysts. New J. Chem. 2010, 34, 1217-1222.