Chiral fullerenes from asymmetric catalysis

Accounts of Chemical Research

Volumn 47, Issue 8, 2014, Pages 2660-2670

  Maroto, Enrique E ^a   Izquierdo, Marta ^a   Reboredo, Silvia ^a   Marco Martínez, Juan ^a   Filippone, Salvatore ^a   Martín, Nazario ^a,b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906242091     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500201b     Document Type: Article

References (46)

1. 60: Buckminsterfullerene Nature 1985, 318, 162-163
2. Fullerenes: From Synthesis to Optoelectronic Properties; Guldi, D. M.; Martín, N., Eds.; Kluwer: Dordrecht, The Netherlands, 2002.
3. 2) Allotrope of Carbon Nature 1991, 353, 149-153
4. Thilgen, C.; Gosse, I.; Diederich, F. Chirality in Fullerene Chemistry Top. Stereochem. 2003, 23, 1-124
5. Thilgen, C.; Diederich, F. Structural Aspects of Fullerene Chemistry: A Journey through Fullerene Chirality Chem. Rev. 2006, 106, 5049-5135
6. Illescas, B.; Martín, N.; Poater, J.; Solà, M.; Aguado, G. P.; Ortuño, R. M. Diastereoselective Synthesis of Fulleropyrrolidines from Suitably Functionalized Chiral Cyclobutanes J. Org. Chem. 2005, 70, 6929-6932
7. Bianco, A.; Maggini, M.; Scorrano, G.; Toniolo, C.; Marconi, G.; Villani, C.; Prato, M. Synthesis, Chiroptical Properties, and Configurational Assignment of Fulleroproline Derivatives and Peptides J. Am. Chem. Soc. 1996, 118, 4072-4080
8. 60 Derivative with a Chiral Addition Pattern Angew. Chem., Int. Ed. Engl. 1996, 35, 2101-2103
9. Guerra, S.; Schillinger, F.; Sigwalt, D.; Holler, M.; Nierengarten, J.-F. Synthesis of Optically Pure [60]fullerene e, e, e -Tris Adducts Chem. Commun. 2013, 49, 4752-4754
10. 60 with an Inherent Chiral Addition Pattern Chem.-Eur. J. 1998, 4, 344-356
11. 2-Symmetric Chiral [60]fullerene- Bisadducts J. Am. Chem. Soc. 2004, 126, 11711-11717
12. Friedman, S. H.; Ganapathi, P. S.; Rubin, Y.; Kenyon, G. L. Optimizing the Binding of Fullerene Inhibitors of the HIV-1 Protease through Predicted Increases in Hydrophobic Desolvation J. Med. Chem. 1998, 41, 2424-2429
13. Zhu, Z.; Schuster, D. I.; Tuckerman, M. E. Molecular Dynamics Study of the Connection between Flap Closing and Binding of Fullerene-Based Inhibitors of the HIV-1 Protease Biochemistry 2003, 42, 1326-1333
14. Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylide-A Simple Approach to Optically Active Highly Functionalized Proline Derivatives Angew. Chem., Int. Ed. 2002, 41, 4236-4238
15. For a recent review, see: Adrio, J.; Carretero, J. C. Novel Dipolarophiles and Dipoles in the Metal-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides Chem. Commun. 2011, 47, 6784-6794
16. 60: Synthesis, Characterization, and Functionalization of Fullerene Pyrrolidines J. Am. Chem. Soc. 1993, 115, 9798-9799
17. Prato, M.; Maggini, M. Fulleropyrrolidines: A Family of Full-Fledged Fullerene Derivatives Acc. Chem. Res. 1998, 31, 519-526
18. Wu, S.-H.; Sun, W.-Q.; Zhang, D.-W.; Shu, L.-H.; Wu, H.-M.; Xu, J.-F.; Lao, X.-F. 1,3-Dipolar Cycloaddition of Several Azomethine Ylides to [60]fullerene: Synthesis of Derivatives of 2′,5′-dihydro-1′ H -pyrrolo[3′,4′:1,2][60]fullerene J. Chem. Soc., Perkin Trans. 1 1998, 1733-1738
19. Pantarotto, D.; Bianco, A.; Pellarini, F.; Tossi, A.; Giangaspero, A.; Zelezetsky, I.; Briand, J.-P.; Prato, M. Solid-Phase Synthesis of Fullerene-Peptides J. Am. Chem. Soc. 2002, 124, 12543-12549
20. Filippone, S.; Maroto, E. E.; Martín-Domenech, A.; Suárez, M.; Martín, N. An Efficient Approach to Chiral Fullerene Derivatives by Catalytic Enantioselective 1,3-Dipolar Cycloadditions Nat. Chem. 2009, 1, 578-582
21. Maroto, E. E.; Filippone, S.; Martín-Domenech, A.; Suárez, M.; Martín, N. Switching the Stereoselectivity: (Fullero)Pyrrolidines "a la Carte" J. Am. Chem. Soc. 2012, 134, 12936-12938
22. 60 J. Am. Chem. Soc. 2014, 136, 705-712
23. Marco-Martínez, J.; Reboredo, S.; Izquierdo, M.; Marcos, V.; López, J. L.; Filippone, S.; Martín, N. Enantioselective Cycloaddition of Münchnones onto [60]fullerene: Organocatalysis versus Metal Catalysis J. Am. Chem. Soc. 2014, 136, 2897-2904
24. 2-Symmetric trans -2,5-Disubstituted Fulleropyrrolidine Tetrahedron Lett. 1998, 39, 4187-4190
25. Gothelf, K. V.; Jorgensen, K. A. Asymmetric 1,3-Dipolar Cycloaddition Reactions Chem. Rev. 1998, 98, 863-909
26. Fisk, J. S.; Mosey, R. A.; Tepe, J. J. The Diverse Chemistry of Oxazol-5-(4 H)-ones Chem. Soc. Rev. 2007, 36, 1432-1440
27. 1-Pyrrolines: exo -Selective 1,3-Dipolar Cycloaddition Reactions with Azlactones J. Am. Chem. Soc. 2004, 126, 12776-12777
28. Melhado, A. D.; Luparia, M.; Toste, F. D. Au(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Münchnones with Electron-Deficient Alkenes J. Am. Chem. Soc. 2007, 129, 12638-12639
29. f,s A (f = fullerene; s = systematic numbering) depend on whether the contiguous numbering of the cage is clockwise or anticlockwise. For IUPAC nomenclature and numbering of fullerenes, see: Cozzi, F.; Powell, W. H.; Thilgen, C. Numbering of Fullerenes Pure Appl. Chem. 2005, 77, 843-923
30. 70: Evidence for Bond Delocalization in Fullerenes J. Am. Chem. Soc. 1998, 120, 2337-2342
31. 70 J. Org. Chem. 1995, 60, 6496-6498
32. Molecular Orbitals and Organic Chemical Reactions; Fleming, I., Ed.; Wiley: Chichester, U.K., 2010.
33. 70 Angew. Chem., Int. Ed. 2011, 50, 6060-6064
34. Chai, Y.; Guo, T.; Jin, C.; Haufler, R. E.; Chibante, L. P. F.; Fure, J.; Wang, L.; Alford, J. M.; Smalley, R. E. Fullerenes with Metals Inside J. Phys. Chem. 1991, 95, 7564-7568
35. Lu, X.; Akasaka, T.; Nagase, S. Chemistry of Endohedral Metallofullerenes: The Role of Metals Chem. Commun. 2011, 47, 5942-5957
36. 72 Having a Non-IPR Carbon Cage J. Am. Chem. Soc. 2006, 128, 14228-14229
37. Sawai, K.; Takano, Y.; Izquierdo, M.; Filippone, S.; Martín, N.; Slanina, Z.; Mizorogi, N.; Waelchli, M.; Tsuchiya, T.; Akasaka, T.; Nagase, S. Enantioselective Synthesis of Endohedral Metallofullerenes J. Am. Chem. Soc. 2011, 133, 17746-17752
38. 60 Chem. Commun. 2014, 50, 740-742
39. Special issue on organocatalysis: Chem. Rev. 2007, 107 (12), 5413-5883.
40. 60 Angew. Chem., Int. Ed. 2013, 52, 5115-5119
41. Zhang, C.; Lu, X. Phosphine-Catalyzed Cycloaddition of 2,3-Butadienoates or 2,3-Butynoates with Electron-Deficient Olefins. A Novel [3 + 2] Annulation Approach to Cyclopentenes J. Org. Chem. 1995, 60, 2906-2908
42. Donovan, B. F. O.; Hitchcock, P. B.; Meidine, M. F.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. Phosphine-Catalysed Cycloaddition of Buta-2,3-dienoates and But-2-ynoates to [60]fullerene Chem. Commun. 1997, 81
43. Xi, Y.; Shi, X. Cinchonine and Thiourea Chem. Commun. 2013, 49, 8583-8585
44. Alemán, J.; Parra, A.; Jiang, H.; Jørgensen, K. A. Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis Chem.-Eur. J. 2011, 17, 6890-6899
45. Connon, S. J. Asymmetric Catalysis with Bifunctional Cinchona Alkaloid-Based Urea and Thiourea Organocatalysts Chem. Commun. 2008, 2499-2510
46. Enders, D.; Niemeier, O.; Henseler, A. Organocatalysis by N-Heterocyclic Carbenes Chem. Rev. 2007, 107, 5606-5655