An inherently chiral calix[4]crown carboxylic acid in the 1,2-alternate conformation

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 74, Issue 1-4, 2012, Pages 277-284

  Xia, Yu Xiang ^a   Zhou, Hao Hui ^b   Shi, Jiao ^a   Li, Si Zhe ^a   Zhang, Min ^a   Luo, Jun ^a   Xiang, Guang Ya ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

1,2 Alternate; Calix 4 arene; Chiral recognition; Inherently chiral; Resolution

Indexed keywords

EID: 84864433453     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-012-0111-2     Document Type: Article

References (46)

1. F Sansone S Barboso A Casnati D Sciotto R Ungaro 1999 A new chiral rigid cone water soluble peptidocalix[4]arene and its inclusion complexes with α-amino acids and aromatic ammonium cations Tetrahedron Lett. 40 4741 4744 10.1016/S0040-4039(99)00838-2 1:CAS:528:DyaK1MXjvVShtL0%3D (Pubitemid 29274051)
2. AM Rincón P Prados J de Mendoza 2001 A calix[4]arene ureidopeptide dimer self-assembled through two superposed hydrogen bond arrays J. Am. Chem. Soc. 123 3493 3498 10.1021/ja0036054 (Pubitemid 32884583)
3. YS Zheng C Zhang 2004 Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure αβ-amino alcohol groups Org. Lett. 6 1189 1192 10.1021/ol036122o 1:CAS:528: DC%2BD2cXitVyjsr4%3D (Pubitemid 38692020)
4. C Bonini L Chiummiento M Funicello MT Lopardo P Lupattelli A Laurita A Cornia 2008 Novel chiral calix[4]arenes by direct asymmetric epoxidation reaction J. Org. Chem. 73 4233 4236 10.1021/jo800301m 1:CAS:528: DC%2BD1cXkvF2mtbg%3D (Pubitemid 351812929)
5. HN Demirtas S Bozkurt M Durmaz M Yilmaz A Sirit 2009 Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives Tetrahedron 65 3014 3018 10.1016/j.tet.2009.01.087 1:CAS:528: DC%2BD1MXjt1art7c%3D
6. 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
7. DA Fulton JF Stoddart 2001 Neoglycoconjugates based on cyclodextrins and calixarenes Bioconj Chem. 12 655 672 10.1021/bc0100410 1:CAS:528: DC%2BD3MXmtFGjurk%3D (Pubitemid 32925867)
8. I Bitter É Koszegi A Grün P Bakó K Pál A Grofcsik M Kubinyi B Balázs G Tóth 2003 Synthesis of chiral 1,3-calix[4](crown-6) ethers as potential mediators for asymmetric recognition processes Tetrahedron Asymmetry 14 1025 1035 10.1016/S0957-4166(03)00174-5 1:CAS:528:DC%2BD3sXisleisLY%3D (Pubitemid 36401591)
9. 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 325 65 72 10.1016/j.molcata.2010. 03.034 1:CAS:528:DC%2BC3cXmsVOjtr0%3D
10. V Böhmer D Kraft M Tabatabai 1994 Inherently chiral calixarenes J. Incl. Phenom. Mol. Recognit. Chem. 19 17 39 10.1007/BF00708972
11. 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
12. Vysotsky, M.; Schmidt, C.; Böhmer, V.: Chirality in calixarenes and calixarene assemblies. In: Gokel, G.W. (ed.) Adv. Supramol. Chem.; vol. 7, pp. 139-233. JAI Press, Stanford (2000)
13. AD Cort L Mandolini C Pasquini L Schiaffino 2004 "Inherent chirality" and curvature New J. Chem. 28 1198 1199 10.1039/b404388j (Pubitemid 39457452)
14. 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)
15. n-symmetric calixarenes and resorcinarenes Supramol. Chem. 22 13 39 10.1080/10610270902980663
16. 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
17. S-Y Li Y-W Xu J-M Liu C-Y Su 2011 Inherently chiral calixarenes: synthesis, optical resolution, chiral recognition and asymmetric catalysis Int. J. Mol. Sci. 12 429 455 10.3390/ijms12010429 1:CAS:528:DC%2BC3MXhtFOhsrY%3D
18. Y-S Zheng J Luo 2011 Inherently chiral calixarenes: a decade's review J. Incl. Phenom. Macrocycl. Chem. 71 35 56 10.1007/s10847-011-9935-4 1:CAS:528:DC%2BC3MXhtFyksbnM
19. 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)
20. 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
21. 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
22. 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
23. S Shirakawa T Kimura S 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
24. 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
25. 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)
26. 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)
27. 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)
28. 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)
29. 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)
30. VI Boyko AV Yakovenko YuI 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
31. 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
32. Z-X Xu C Zhang Z-T Huang C-F 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
33. V 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
34. VI Boyko A Shivanyuk VV Pyrozhenko RI Zubatyuk OV Shishikin 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)
35. 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
36. 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
37. Z-X Xu C Zhang Y Yang C-F Chen Z-T Huang 2008 Effective nonenzymatic kinetic resolution of racemic m-nitrosubstituted inherently chiral aminocalix[4]arenes Org. Lett. 10 477 479 10.1021/ol702884u 1:CAS:528: DC%2BD1cXjt1ejsw%3D%3D
38. SA Herbert GE Arnott 2009 An asymmetric ortholithiation approach to inherently chiral calix[4]arenes Org. Lett. 11 4986 4989 10.1021/ol902238p 1:CAS:528:DC%2BD1MXht1Cjs7rP
39. 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
40. 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)
41. 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)
42. 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)
43. 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)
44. G Ferguson AJ Lough A Notti S Pappalardo MF Parisi A Petringa 1998 1,2-Bridged calix[4]arene monocrowns and biscrowns in the 1,2-alternate conformation J. Org. Chem. 63 9703 9710 10.1021/jo9810516 1:CAS:528: DyaK1cXns1aht7w%3D (Pubitemid 29035121)
45. A Arduini L Domiano A Pochini A Secchi R Ungaro F Ugozzoli O Struck W Verboom DN Reinhoudt 1997 Synthesis of 1,2-bridged calix[4]arene-biscrowns in the 1,2-alternate conformation Tetrahedron 53 3767 3776 10.1016/S0040-4020(97) 00097-5 1:CAS:528:DyaK2sXhvFyns7g%3D (Pubitemid 27110875)
46. F Narumi T Hattori N Matsumura T Onodera H Katagiri C Kabuto H Kameyama S Miyano 2004 Synthesis of an inherently chiral O, O'-bridged thiacalix[4]crowncarboxylic acid and its application to a chiral solvating agent Tetrahedron 60 7827 7833 10.1016/j.tet.2004.06.074 1:CAS:528: DC%2BD2cXmsVajtr8%3D (Pubitemid 39078199)