Asymmetric synthesis of hexahydropyrrolo-isoquinolines by an organocatalytic three-component reaction

Chemistry - A European Journal

Volumn 18, Issue 10, 2012, Pages 2773-2776

  Fraile, Alberto ^a   Scarpino Schietroma, Daniele M ^a   Albrecht, Anna ^a   Davis, Rebecca L ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

asymmetric catalysis; azomethine ylides; cycloaddition; organocatalysis; pyrroloisoquinolines

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC REACTION; ASYMMETRIC SYNTHESIS; AZOMETHINE YLIDES; LIFE-SCIENCES; OPTICALLY ACTIVE; ORGANOCATALYSIS; ORGANOCATALYTIC; PYRROLOISOQUINOLINES; THREE COMPONENT REACTIONS; THREE-COMPONENT; UNSATURATED ALDEHYDES;

ALDEHYDES; AROMATIC POLYMERS; CATALYSIS; CYCLOADDITION; KETONES; ORGANIC COMPOUNDS; REACTION KINETICS;

ENANTIOSELECTIVITY;

ALDEHYDE; ESTER; IMINE; ISOQUINOLINE DERIVATIVE; KETONE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALDEHYDES; CATALYSIS; CYCLIZATION; ESTERS; IMINES; ISOQUINOLINES; KETONES; MOLECULAR STRUCTURE; PYRROLES;

EID: 84857565386     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200108     Document Type: Article

References (61)

1. A. G. Mikhailovskii, V. S. Shklyaev, Chem. Heterocycl. Compd. 1997, 33, 243.
2. M. Ozawa, S. Kawamata, T. Etoh, M. Hayashi, K. Komiyama, A. Kishida, C. Kuroda, A. Ohsaki, Chem. Pharm. Bull. 2010, 58, 1119
3. F. Zhang, N. S. Simpkins, A. J. Blake, Org. Biomol. Chem. 2009, 7, 1963
4. S. F. Dyke, S. N. Quessy, in The Alkaloids, Vol. 18 (Ed.: , R. G. A. Rodrigo,), Academic Press, New York, 1981, pp. 1-98.
5. D. Pla, F. Albericio, M. Úlvarez, Med. Chem. Commun. 2011, 2, 689
6. L. Shen, X. Yan, B. Yang, Q. He, Y. Hu, Eur. J. Med. Chem. 2010, 45, 11
7. D. Baunbæk, N. Trinkler, Y. Ferandin, O. Lozach, P. Ploypradith, S. Rucirawat, F. Ishibashi, M. Iwao, L. Meijer, Mar. Drugs 2008, 6, 514.
8. T. R. Wu, J. M. Chong, J. Am. Chem. Soc. 2006, 128, 9646
9. J. Szawkało, A. Zawadzka, K. Wojtasiewicz, A. Leniewski, J. Drabowicz, Z. Czarnocki, Tetrahedron: Asymmetry 2005, 16, 3619.
10. J. M. Keith, L. A. Gomez, A. J. Barbier, S. J. Wilson, J. D. Boggs, B. Lord, C. Mazur, L. Aluisio, T. W. Lovenberg, N. I. Carruthers, Bioorg. Med. Chem. Lett. 2007, 17, 4374
11. J. M. Keith, L. A. Gomez, R. L. Wolin, A. J. Barbier, S. J. Wilson, J. D. Boggs, C. Mazur, I. C. Fraser, B. Lord, L. Aluisio, T. W. Lovenberg, N. I. Carruthers, Bioorg. Med. Chem. Lett. 2007, 17, 2603.
12. C. Yu, Y. Zhang, S. Zhang, H. Li, W. Wang, Chem. Commun. 2011, 47, 1036
13. M. Rueping, D. Leonori, T. Poisson, Chem. Commun. 2011, 47, 9615
14. Y.-Q. Zou, L.-Q. Lu, L. Fu, N.-J. Chang, J. Rong, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2011, 123, 7309
15. Angew. Chem. Int. Ed. 2011, 50, 7171
16. Y. Han, H. Hou, Q. Fu, C.-G. Yan, Tetrahedron 2011, 67, 2313
17. H. Adams, T. M. Elsunaki, I. Ojea-Jiménez, S. Jones, A. J. H. M. Meijer, J. Org. Chem. 2010, 75, 6252
18. J. Tõth, L. Váradi, A. Dancsõ, G. Blaskõ, L. Toke, M. Nyerges, Synthesis 2009, 4149
19. D. Basavaiah, B. Devendar, D. V. Lenin, T. Satyanarayana, Synlett 2009, 411
20. A. K. Verma, T. Kesharwani, J. Singh, V. Tandon, R. C. Larock, Angew. Chem. 2009, 121, 1158
21. Angew. Chem. Int. Ed. 2009, 48, 1138
22. I. Yavari, M. Piltan, L. Moradi, Tetrahedron 2009, 65, 2067.
23. N. Landoni, G. Lesma, A. Sacchetti, A. Silvani, J. Org. Chem. 2007, 72, 9765
24. A Silvani, J. Org. Chem. 2007, 72, 9765
25. S. M. Allin, S. N. Gaskell, J. M. R. Towler, P. C. B. Page, B. Saha, M. J. McKenzie, W. P. Martin, J. Org. Chem. 2007, 72, 8972
26. E. García, S. Arrasate, E. Lete, N. Sotomayor, J. Org. Chem. 2005, 70, 10368
27. D. Mostowicz, R. Wõjcik, G. Dołȩga, Z. Kałuza, Tetrahedron Lett. 2004, 45, 6011
28. Z. Kałuża, D. Mostowicz, Tetrahedron: Asymmetry 2003, 14, 225
29. V. Jullian, J. Quirion, H. Husson, Eur. J. Org. Chem. 2000, 1319.
30. M. Miyazaki, N. Ando, K. Sugai, Y. Seito, H. Fukuoka, T. Kanemitsu, K. Nagata, Y. Odanaka, K. T. Nakamura, T. Itoh, J. Org. Chem. 2011, 76, 534
31. T. Itoh, K. Nagata, M. Yokoya, M. Michiko, K. Kameoka, S. Nakamura, A. Ohsawa, Chem. Pharm. Bull. 2003, 51, 951.
32. G.-H. Hou, J.-H. Xie, P.-C. Yan, Q.-L. Zhou, J. Am. Chem. Soc. 2009, 131, 1366.
33. J. L. García Ruano, A. Fraile, M. R. Martín, G. González, C. Fajardo, A. M. Martín-Castro, J. Org. Chem. 2011, 76, 3296.
34. J. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6784
35. C. Nájera, J. M. Sansano, Monatsh. Chem. 2011, 142, 659
36. C. Nájera, J. M. Sansano, M. Yus, J. Braz. Chem. Soc. 2010, 21, 377.
37. A. Moyano, R. Rios, Chem. Rev. 2011, 111, 4703.
38. N. Fernández, L. Carrillo, J. L. Vicario, D. Badía, E. Reyes, Chem. Commun. 2011, 47, 12313
39. S. Lin, L. Deiana, G.-L. Zhao, J. Sun, A. Cordova, Angew. Chem. 2011, 123, 7766
40. Angew. Chem. Int. Ed. 2011, 50, 7624
41. J. L. Vicario, S. Reboredo, D. Badia, L. Carrillo, Angew. Chem. 2007, 119, 5260
42. Angew. Chem. Int. Ed. 2007, 46, 5168.
43. D. J. Ramõn, M. Yus, Angew. Chem. 2005, 117, 1628
44. Angew. Chem. Int. Ed. 2005, 44, 1602
45. J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
46. M. Nyerges, B. Somfai, J. Tõth, L. Toke, A. Dancsõ, G. Blaskõ, Synthesis 2005, 2039.
47. K. L. Jensen, G. Dickmeiss, H. Jiang, Ś. Albrecht, K. A. Jørgensen, Acc. Chem. Res. 2012, DOI
48. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804
49. Angew. Chem. Int. Ed. 2005, 44, 794
50. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284
51. Angew. Chem. Int. Ed. 2005, 44, 4212.
52. P. J. Stang, F. Diederich, Modern Acetylene Chemistry, VCH, Weinheim, 1995. See also
53. K. A. Kalesh, H. Shi, J. Ge, S. Q. Yao, Org. Biomol. Chem. 2010, 8, 1749
54. J. C. Jewetta, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272
55. R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874.
56. S. Ohira, Synth. Commun. 1989, 19, 561
57. S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521
58. G. J. Roth, B. Liepold, S. G. Müller, H. J. Bestmann, Synthesis 2004, 59.
59. S. G. Levine, J. Am. Chem. Soc. 1958, 80, 6150.
60. Calculations were performed with GAUSSIAN09. Geometries were optimized without symmetry constraints at the M06-2X/6-31G+(d,p) (see ref., Y. Zhao, D. Truhlar, Theor. Chem. Acc. 2008, 120, 215) level of theory in the gas phase. See Supporting Information for the complete references on theoretical methods.
61. -1.