Inherently chiral calixarenes: A decade's review

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 71, Issue 1-2, 2011, Pages 35-56

  Zheng, Yan Song ^a   Luo, Jun ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Calixarene; Enantioselective recognition; Inherently chiral; Optical resolution; Organocatalyst; Stereoselective synthesis

Indexed keywords

EID: 80054927195     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-9935-4     Document Type: Review

References (78)

1. A Sirit M Yilmaz 2009 Chiral calixarenes Turk. J. Chem. 33 159 200 1:CAS:528:DC%2BD1MXnsVCmsbg%3D
2. V Gopalsamuthiram AV Predeus RH Huang WD Wulff 2009 Optically active calixarenes conduced by methylene substitution J. Am. Chem. Soc. 131 18018 18019 10.1021/ja905990u 1:CAS:528:DC%2BD1MXhsVKhs7rK
3. V Gopalsamuthiram R Huang WD Wulff 2010 The synthesis of optically active calix[4]arenes with one or three substituents on the methylene bridges Chem. Commun. 46 8213 8215 10.1039/c0cc02689a 1:CAS:528:DC%2BC3cXhtlentbjE
4. V Böhmer D Kraft M Tabatabai 1994 Inherently chiral calixarenes J. Incl. Phenom. Mol. Recognit. Chem. 19 17 39 10.1007/BF00708972
5. AD Cort L Mandolini C Pasquini L Schiaffino 2004 "Inherent chirality" and curvature New J. Chem. 28 1198 1199 10.1039/b404388j (Pubitemid 39457452)
6. A Szumna 2010 Inherently chiral concave molecules-from synthesis to applications Chem. Soc. Rev. 39 4274 4285 10.1039/b919527k 1:CAS:528: DC%2BC3cXhtlShtbzK
7. G Seeber BEF Tiedemann KN Raymond 2006 Supramolecular chirality in coordination chemistry Top. Curr. Chem. 265 147 183 10.1007/128-033 1:CAS:528:DC%2BD28Xnsl2gtLs%3D (Pubitemid 44420762)
8. J Rebek Jr 2000 Host-guest chemistry of calixarene capsules Chem. Commun. 36 637 643 10.1039/a910339m (Pubitemid 30225479)
9. MA Mateos-Timoneda 2004 Supramolecular chirality of self-assembled systems in solution Chem. Soc. Rev. 33 363 372 10.1039/b305550g 1:CAS:528:DC%2BD2cXmtVWgtbY%3D (Pubitemid 39163827)
10. S Vázquez-Campos M Crego-Calama DN Reinhoudt 2007 Supramolecular chirality of hydrogen-bonded rosette assemblies Supramol. Chem. 19 95 106 10.1080/10610270600981716
11. Y Rudzevich V Rudzevich V Böhmer 2010 Selective dimerisation of tetraurea calix[4]arenes Supramol. Chem. 22 717 725 10.1080/10610278.2010.500730 1:CAS:528:DC%2BC3cXhsVGku7vJ
12. N Le Poul B Douziech J Zeitouny G Thiabaud H Colas F Conan N Cosquer I Jabin C Lagrost P Hapiot O Reinaud Y Le Mest 2009 Mimicking the protein access channel to a metal center: effect of a funnel complex on dissociative versus associative copper redox chemistry J. Am. Chem. Soc. 131 17800 17807 10.1021/ja9055905 1:CAS:528:DC%2BD1MXhsVWrtbzL
13. Y Kubo S Maeda S Tokita M Kubo 1996 Colorimetric chiral recognition by a molecular sensor Nature 382 522 524 10.1038/382522a0 1:CAS:528: DyaK28XkvFGjt74%3D (Pubitemid 26260689)
14. S Liu CA Sandoval 2010 Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives J. Mol. Catal. A Chem. 325 65 72 10.1016/j.molcata.2010.03.034 1:CAS:528:DC%2BC3cXmsVOjtr0%3D
15. KH Krawinkler NM Maier R Ungaro F Sansone A Casnati W Lindner 2003 Novel cinchona carbamate selectors with complementary enantioseparation characteristics for N-acylated amino acids Chirality 15 S17 S29 10.1002/chir.10257 1:CAS:528:DC%2BD3sXmt1GgsLg%3D (Pubitemid 36935496)
16. YS Zheng C Zhang 2004 Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure α, β-amino alcohol groups Org. Lett. 6 1189 1192 10.1021/ol036122o 1:CAS:528: DC%2BD2cXitVyjsr4%3D (Pubitemid 38692020)
17. AB Salem J-B Regnouf-de-Vains 2001 Synthesis and characterisation of a new pod and based on a calixarene and a β-lactam Tetrahedron Lett. 42 7033 7036 10.1016/S0040-4039(01)01319-3 (Pubitemid 32835147)
18. R Ludwig 2005 Calixarenes for biochemical recognition and separation Microchim. Acta 152 1 19 10.1007/s00604-005-0422-8 1:CAS:528:DC%2BD2MXht1Smtb7I (Pubitemid 41613784)
19. F Sansone L Baldini A Casnati R Ungaro 2010 Calixarenes: from biomimetic receptors to multivalent ligands for biomolecular recognition New J. Chem. 34 2715 2728 10.1039/c0nj00285b 1:CAS:528:DC%2BC3cXhsVGrs7bO
20. H Otsuka S Shinkai 1996 Stereochemical control of calixarenes useful as rigid and conformationally diversiform platforms for molecular design Supramol. Sci. 3 189 205 10.1016/S0968-5677(96)00038-7
21. Vysotsky, M., Schmidt, C., Böhmer, V.: Chirality in calixarenes and calixarene assemblies. In: Gokel, G.W. (ed.) Advances in Supramolecular Chemistry, vol. 7, pp. 139-233. JAI Press, Stanford (2000)
22. S Cherenok J-P Dutasta V Kalchenko 2006 Phosphorus-containing chiral macrocycles Curr. Org. Chem. 10 2307 2331 10.2174/138527206778992725 1:CAS:528:DC%2BD28Xht1yjtrjF (Pubitemid 44873705)
23. n-symmetric calixarenes and resorcinarenes Supramol. Chem. 22 13 39 10.1080/10610270902980663 1:CAS:528:DC%2BC3cXjsFGitr4%3D
24. KH No CD Gutsche 1982 Calixarenes. 8. Short, stepwise synthesis of p-phenylcalix[4]arene, p-phenyl-p-tert-butylcalix[4]arene, and derived products J. Org. Chem. 47 2713 2719 10.1021/jo00135a006
25. MA Tairov MO Vysotsky OI Kalchenko VV Pirozhenko VI Kalchenko 2002 Symmetrical and inherently chiral water-soluble calix[4]arenes bearing dihydroxyphosphoryl groups J. Chem. Soc., Perkin Trans. 1 31 1405 1411 10.1039/b110691k (Pubitemid 35187090)
26. Y-D Cao J Luo Q-Y Zheng C-F Chen M-X Wang Z-T Huang 2004 Preparation of both antipodes of enantiopure inherently chiral calix[4]crowns J. Org. Chem. 69 206 208 10.1021/jo0354185 1:CAS:528:DC%2BD3sXps1Snu7k%3D (Pubitemid 38040829)
27. J Luo Q-Y Zheng C-F Chen Z-T Huang 2005 Synthesis and optical resolution of a series of inherently chiral calix[4]crowns with cone and partial cone conformations Chem. Eur. J. 11 5917 5928 10.1002/chem.200500272 1:CAS:528:DC%2BD2MXhtFCgsrvF (Pubitemid 41454691)
28. J Luo Q-Y Zheng C-F Chen Z-T Huang 2005 Facile synthesis and optical resolution of inherently chiral fluorescent calix[4]crowns: enantioselective recognition towards chiral leucinol Tetrahedron 61 8517 8528 10.1016/j.tet.2005.06.015 1:CAS:528:DC%2BD2MXntVCgtbw%3D (Pubitemid 41058696)
29. S-Y Li Q-Y Zheng C-F Chen Z-T Huang 2005 Preparation of enantiopure inherently chiral calix[5]arenes Tetrahedron Asymmetry 16 641 645 10.1016/j.tetasy.2004.11.080 1:CAS:528:DC%2BD2MXht1Cks7c%3D (Pubitemid 40247652)
30. R Arnecke V Böhmer G Ferguson S Pappalardo 1996 Inherently chiral derivatives of calix[5]crowns Tetrahedron Lett. 37 1497 1500 10.1016/0040-4039(96)00048-2 1:CAS:528:DyaK28XhsFWqsro%3D (Pubitemid 26080107)
31. JJ Gonzalez PM Nieto P Prados AM Echavarren J de Mendoza 1995 Calix[4]arene sulfonates: palladium-catalyzed intermolecular migration of sulfonyl groups and isolation of a calix[4]arene in a chiral 1,2-alternate conformation J. Org. Chem. 60 7419 7423 10.1021/jo00128a012 1:CAS:528: DyaK2MXovF2gtLg%3D
32. F Narumi W Yamabuki T Hattori H Kameyama S Miyano 2003 Synthesis and optical resolution of an anti-O,O′-dialkylated calix[4]arene Chem. Lett. 32 320 321 10.1246/cl.2003.320 1:CAS:528:DC%2BD3sXjtVWrsbY%3D (Pubitemid 36843181)
33. F Narumi T Hattori W Yamabuki C Kabuto H Kameyama 2005 Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods Tetrahedron Asymmetry 16 793 800 10.1016/j.tetasy.2004.11.095 1:CAS:528:DC%2BD2MXhtlShtrk%3D (Pubitemid 40253536)
34. AW Kleij B Souto CJ Pastor P Prados J de Mendoza 2003 Unexpected single-step formation of 1,2-anti-heterodisubstituted calix[4]arenes upon alkylation of a tribenzoyl precursor J. Org. Chem. 68 8711 8714 10.1021/jo035150h 1:CAS:528:DC%2BD3sXns1OgsLs%3D (Pubitemid 37329138)
35. S Shirakawa A Moriyama S Shimizu 2007 Design of a novel inherently chiral calix[4]arene for chiral molecular recognition Org. Lett. 9 3117 3119 10.1021/ol071249p 1:CAS:528:DC%2BD2sXns1Ohtb0%3D
36. S Shirakawa A Moriyama S Shimizu 2008 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 10.1002/ejoc.200800850
37. S Shirakawa T Kimura S-i Murata S Shimizu 2009 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. 74 1288 1296 10.1021/jo8024412 1:CAS:528:DC%2BD1cXhsFais7zM
38. S Shirakawa S Shimizu 2009 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 1916 1924 10.1002/ejoc.200801288
39. S Shirakawa S Shimizu 2010 Improved design of inherently chiral calix[4]arenes as organocatalysts New J. Chem. 34 1217 1222 10.1039/b9nj00685k 1:CAS:528:DC%2BC3cXmslWhs7g%3D
40. B Colasson O Reinaud 2008 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. 130 15226 15227 10.1021/ja803878g 1:CAS:528:DC%2BD1cXhtlWqtLrE
41. J Luo L-C Shen W-S Chung 2010 Inherently chiral biscalix[4]arenes: design and syntheses J. Org. Chem. 75 464 467 10.1021/jo9023792 1:CAS:528: DC%2BD1MXhsFKgurjF
42. R Miao Q-Y Zheng C-F Chen Z-T Huang 2005 Efficient syntheses and resolutions of inherently chiral calix[4]quinolines in the cone and partial-cone conformation J. Org. Chem. 70 7662 7671 10.1021/jo050980b 1:CAS:528: DC%2BD2MXotVSltb0%3D (Pubitemid 41318528)
43. R Miao Z-X Xu Z-T Huang C-F Chen 2009 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 B. Chem. 52 505 512 10.1007/s11426-009-0002-6 1:CAS:528:DC%2BD1MXksFaks7c%3D
44. M Mastalerz W Hüggenberg G Dyker 2006 Photochemistry of styrylcalix[4]arenes Eur. J. Org. Chem. 2006 3977 3987 10.1002/ejoc.200600265
45. W Verboom PJ Bodewes G van Essen P Timmerman GJ van Hummel S Harkema DN Reinhoudt 1995 A novel approach to inherently chiral calix[4]arenes by direct introduction of a substituent at the meta position Tetrahedron 51 499 512 10.1016/0040-4020(94)00911-D 1:CAS:528:DyaK2MXjtlKisLw%3D
46. III complexes containing a calix[4]arene unit as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes Eur. J. Org. Chem. 2005 3562 3570 10.1002/ejoc.200500138 (Pubitemid 41187273)
47. GML Consoli F Cunsolo C Geraci P Neri 2005 Synthesis of p-tert-butyl-5,5′-bicalix[4]arene and access to 5,5′-bicalix[4] arenes functionalized at the upper rim Lett. Org. Chem. 2 252 257 10.2174/1570178053765357 1:CAS:528:DC%2BD2MXkt1Whtrc%3D
48. F Troisi T Pierro C Gaeta M Carratù P Neri 2009 Appending aromatic moieties at the para- and meta-position of calixarene phenol rings via p-bromodienone route Tetrahedron Lett. 50 4416 4419 10.1016/j.tetlet.2009.05.032 1:CAS:528:DC%2BD1MXnsFCiu70%3D
49. 1 symmetry of chiral auxiliaries in catalytic reactions on metal complexes Tetrahedron 64 1147 1179 10.1016/j.tet.2007.10.078 1:CAS:528:DC%2BD1cXlt1ajsw%3D%3D
50. A Ikeda M Yoshimura P Lhoták S Shinkai 1996 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. 1 25 1945 1950 10.1039/p19960001945 (Pubitemid 126801323)
51. A Ikeda S Shinkai 1993 'Stapled' calix[n]arenes: immobilization of the calix[4]arene conformation by cross-linking on the upper rim J. Chem. Soc. Perkin Trans 1 22 2671 2673 10.1039/p19930002671
52. I Bitter A Grün G Tóth B Balázs G Horváth L Toke 1998 Studies on calix(aza)crowns, II. Synthesis of novel proximal doubly bridged calix[4]arenes by intramolecular ring closure of syn 1,3- and 1,2-ω-chloroalkylamides Tetrahedron 54 3857 3870 10.1016/S0040-4020(98) 00112-4 1:CAS:528:DyaK1cXivV2qsb0%3D (Pubitemid 28139074)
53. SK Sharma CD Gutsche 1999 Synthesis and reactions of calix[4]arene bisanhydrides J. Org. Chem. 64 3507 3512 10.1021/jo9822636 1:CAS:528: DyaK1MXisFGnt7o%3D (Pubitemid 29232955)
54. AW Kleij P Prados J de Mendoza 2004 A fast access to non-symmetrically substituted 1,3-alternate conformers of calix[4]arenes Eur. J. Org. Chem. 2004 2848 2852 10.1002/ejoc.200400161
55. S Shimizu A Moriyama K Kito Y Sasaki 2003 Selective synthesis and isolation of all possible conformational isomers of proximally para-disubstituted calix[4]arene J. Org. Chem. 68 2187 2194 10.1021/jo0267293 1:CAS:528:DC%2BD3sXhtFCgsbw%3D (Pubitemid 36505093)
56. MT Blanda L Edwards R Salazar M Boswell 2006 Synthesis and characterization of an inherently chiral calix[6]arene in the 1,4-alternate conformation Tetrahedron Lett. 47 7081 7084 10.1016/j.tetlet.2006.07.087 1:CAS:528:DC%2BD28XoslChsL4%3D (Pubitemid 44278952)
57. 4 symmetry J. Org. Chem. 55 5665 5667 10.1021/jo00309a001 1:CAS:528:DyaK3cXmtFWmtrs%3D
58. 2-symmetrical endo-calix[4] naphthalene J. Org. Chem. 67 6808 6811 10.1021/jo026045v 1:CAS:528: DC%2BD38XmsFGlsro%3D
59. OG Barton B Neumann H-G Stammler J Mattay 2008 Intramolecular direct arylation in an A, C-functionalized calix[4]arene Org. Biomol. Chem. 6 104 111 10.1039/b713357j 1:CAS:528:DC%2BD2sXhsVantbbO (Pubitemid 350255964)
60. C Dieleman S Steyer C Jeunesse D Matt 2001 Diphosphines based on an inherently chiral calix[4]arene scaffold: synthesis and use in enantioselective catalysis J. Chem. Soc. Dalton Trans. 30 2508 2517 10.1039/b101369f (Pubitemid 35166702)
61. AV Yakovenko VI Boyko O Danylyuk K Suwinska J Lipkowski VI Kalchenko 2007 Diastereoselective lower rim (1S)-camphor sulfonylation as the shortest way to the inherently chiral calix[4]arene Org. Lett. 9 1183 1185 10.1021/ol0628513 1:CAS:528:DC%2BD2sXitVyhsL4%3D
62. VI Boyko AV Yakovenko YI Matvieiev OI Kalchenko OV Shishkin SV Shishkina VI Kalchenko 2008 Regio- and stereoselective 1(S)-camphor sulfonylation of monoalkoxycalix[4]arenes Tetrahedron 64 7567 7573 10.1016/j.tet.2008.05.106 1:CAS:528:DC%2BD1cXnvFykuro%3D
63. VI Boyko YI Matvieiev MA Klyachina OA Yesypenko SV Shishkina OV Shishkin VI Kalchenko 2009 Proximal heteroalkylation of monoalkoxycalix[4]arenes in synthesis of inherently chiral molecules Tetrahedron 65 4220 4227 10.1016/j.tet.2009.03.036 1:CAS:528:DC%2BD1MXltVamtLk%3D
64. VI Boyko A Shivanyuk VV Pyrozhenko RI Zubatyuk OV Shishkin VI Kalchenko 2006 A stereoselective synthesis of asymmetrically substituted calix[4]arene carbamates Tetrahedron Lett. 47 7775 7778 10.1016/j.tetlet.2006.08.095 1:CAS:528:DC%2BD28XhtVWqtL7O (Pubitemid 44441485)
65. MA Kliachyna OA Yesypenko VV Pirozhenko SV Shishkina OV Shishkin VI Boyko VI Kalchenko 2009 Synthesis, optical resolution and absolute configuration of inherently chiral calixarene carboxylic acids Tetrahedron 65 7085 7091 10.1016/j.tet.2009.06.039 1:CAS:528:DC%2BD1MXptVGgt7Y%3D
66. Z-X Xu C Zhang Q-Y Zheng C-F Chen Z-T Huang 2007 A new approach to enantiopure inherently chiral calix[4]arenes: determination of their absolute configurations Org. Lett. 9 4447 4450 10.1021/ol701714q 1:CAS:528: DC%2BD2sXhtVOltbbE
67. Z-X Xu C Zhang Y Yang C-F Chen Z-T Huang 2008 Effective nonenzymatic kinetic resolution of racemic m-nitro-substituted inherently chiral aminocalix[4]arenes Org. Lett. 10 477 479 10.1021/ol702884u 1:CAS:528: DC%2BD1cXjt1ejsw%3D%3D
68. ZX Xu C Zhang ZT Huang CF Chen 2010 Efficient synthesis and resolution of meta-substituted inherently chiral aminocalix[4]arene derivatives Chin. Sci. Bull. 55 2859 2869 10.1007/s11434-010-3121-8
69. Z-X Xu G-K Li C-F Chen Z-T Huang 2008 Inherently chiral calix[4]arene-based bifunctional organocatalysts for enantioselective aldol reactions Tetrahedron 64 8668 8675 10.1016/j.tet.2008.07.001 1:CAS:528:DC%2BD1cXptlyhtbs%3D
70. Z-X Xu Z-T Huang C-F Chen 2009 Synthesis and structures of novel enantiopure inherently chiral calix[4]arene-derived salphen ligands and their transition-metal complexes Tetrahedron Lett. 50 5430 5433 10.1016/j.tetlet.2009. 07.064 1:CAS:528:DC%2BD1MXps1Cjs7w%3D
71. SA Herbert GE Arnott 2009 An asymmetric ortholithiation approach to inherently chiral calix[4]arenes Org. Lett. 21 4986 4989 10.1021/ol902238p
72. SA Herbert GE Arnott 2010 Synthesis of inherently chiral calix[4]arenes: stereocontrol through ligand choice Org. Lett. 12 4600 4603 10.1021/ol101909f 1:CAS:528:DC%2BC3cXhtFKmt7fM
73. N Itzhak SE Biali 2010 Selective functionalization of a single methylene bridge of a calix[6]arene J. Org. Chem. 75 3437 3442 10.1021/jo1005476 1:CAS:528:DC%2BC3cXltFChu74%3D
74. K Kogan SE Biali 2009 Incorporation of substituents at the methylene linkages of the calix[5]arene skeleton J. Org. Chem. 74 7172 7175 10.1021/jo901450x 1:CAS:528:DC%2BD1MXhtVCgt7jM
75. K Kogan I Columbus SE Biali 2008 Functionalization of the methylene bridges of the calix[6]arene scaffold J. Org. Chem. 73 7327 7335 10.1021/jo801187z 1:CAS:528:DC%2BD1cXhtVWmurbI
76. I Columbus SE Biali 2008 Calix[4]arene derivatives monosubstituted at all four methylene bridges J. Org. Chem. 73 2598 2606 10.1021/jo702474n 1:CAS:528:DC%2BD1cXis1eku7g%3D (Pubitemid 351482967)
77. PD Harvey 2002 Wide-rim and outer-face functionalizations of calix[4]arene Coord. Chem. Rev. 233-234 289 309 10.1016/S0010-8545(02)00199-6
78. H Iki T Kikuchi S Shinkai 1993 Syntheses and spectral characterizations of tricarbonylchromium complexes of calix[4]arenes J. Chem. Soc. Perkin Trans. 1 22 205 210 10.1039/p19930000205