Pd0-catalyzed three-component tandem double-addition-cyclization reaction: Stereoselective synthesis of cis-pyrrolidine derivatives

Angewandte Chemie - International Edition

Volumn 41, Issue 24, 2002, Pages 4737-4740

  Ma, Shengming ^a   Jiao, Ning ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allenes; Cyclization; Diastereoselectivity; Palladium; Solvent effects

Indexed keywords

HALOGEN COMPOUNDS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DOUBLE ADDITION CYCLIZATION;

CATALYSIS;

2 (2,3 BUTADIENYL)MALONATE; IMINE; MALONIC ACID; ORGANOHALOGEN DERIVATIVE; PALLADIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037122046     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200290033     Document Type: Article

References (50)

1. a) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, John Wiley, New York, 1984; The Chemistry of Ketenes, Allenes, and Related Compounds, Part I (Ed.: S. Patai), Wiley, New York, 1980.
2. a) H. F. Schuster, G. M. Coppola, Allenes in Organic Synthesis, John Wiley, New York, 1984; The Chemistry of Ketenes, Allenes, and Related Compounds, Part I (Ed.: S. Patai), Wiley, New York, 1980.
3. For a review on the palladium-catalyzed chemistry of allenes, see: R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; for a recent highlight, see: A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737; Angew. Chem. Int. Ed. 2000, 39, 3590.
4. For a review on the palladium-catalyzed chemistry of allenes, see: R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; for a recent highlight, see: A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737; Angew. Chem. Int. Ed. 2000, 39, 3590.
5. For a review on the palladium-catalyzed chemistry of allenes, see: R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067; for a recent highlight, see: A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737; Angew. Chem. Int. Ed. 2000, 39, 3590.
6. For some of the most recent publications, see: a) J. Löfstedt, J. Franzén, J.-E. Bäckvall, J. Org. Chem. 2001, 66, 8015;
7. b) W. F. J. Karstens, D. Klomp, F. P. J. T. Rutjes, H. Hiemstra, Tetrahedron 2001, 57, 5123;
8. c) G. Liu, X. Lu, Org. Lett. 2001, 3, 3879;
9. d) P. K. Dieter, H. Yu, Org. Lett. 2001, 3, 3855;
10. e) Y.-H. Ha, S.-K. Kang, Org. Lett. 2002, 4, 1143;
11. f) S.-K. Kang, Y.-H. Ha, B.-S. Ko, Y. Lim, J. Jung, Angew. Chem. 2002, 114, 353; Angew. Chem. Int. Ed. 2002, 41, 343.
12. f) S.-K. Kang, Y.-H. Ha, B.-S. Ko, Y. Lim, J. Jung, Angew. Chem. 2002, 114, 353; Angew. Chem. Int. Ed. 2002, 41, 343.
13. For some of the most recent results from our group, see: a) S. Ma, S. Zhao, J. Am. Chem. Soc. 2001, 123, 5578;
14. b) S. Ma, Z. Shi, Chem. Commun. 2002, 540;
15. c) S. Ma, W. Gao, Synlett 2002, 65;
16. d) S. Ma, D. Duan, Y. Wang, J. Comb. Chem. 2002, 4, 239;
17. e) S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew Chem. Int. Ed. 2002, 41, 1775.
18. e) S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew Chem. Int. Ed. 2002, 41, 1775.
19. a) I. Shimizu, J. Tsuji, Chem. Lett. 1984, 233;
20. b) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1984, 25, 4505.
21. a) B. M. Trost, Science 1991, 254, 1471;
22. b) B. M. Trost, Angew. Chem. 1995, 107, 285; Agew. Chem. Int. Ed. Engl. 1995, 34, 259.
23. b) B. M. Trost, Angew. Chem. 1995, 107, 285; Agew. Chem. Int. Ed. Engl. 1995, 34, 259.
24. a) L. F. Tietze, Chem. Rev. 1996, 96, 115;
25. b) P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195;
26. c) R. A. Bunce, Tetrahedron 1995, 51, 13103.
27. a) D. Enders, C. Thiebes, Pure. Appl. Chem. 2001, 73, 573;
28. b) D. O'hagan, Nat. Prod. Rep. 2000, 17, 435;
29. c) A. R. Pinder, Nat. Prod. Rep. 1992, 9, 17;
30. d) G. Massiot, C. Ddelaude in Alkaloids (Ed.: A. Brossi), Academic Press, New York, 1996, 27, 269.
31. a) J.-E. Bäckvall, H. E. Schink, Z. D. Renko, J. Org. Chem. 1990, 55, 826;
32. b) E. Lee, E. J. Jeong, S. J. Min, S. Hong, J. Lim, S. K. Kim, H. J. Kim, B. G. Chio, K. C. Koo, Org. Lett. 2000, 2, 2169;
33. c) A. Boto, R. Hernández, Y. de León, E. Suárez, J. Org. Chem. 2001, 66, 7796;
34. d) B. Schlummer, J. F. Hartwig, Org. Lett. 2002, 4, 1471.
35. For the Pd(0)-catalyzed coupling-cyclization reaction of γ-allenic amides with aryl or vinyl halides, see: a) S.-K. Kang, K.-J. Kim, Org. Lett. 2001, 3, 511; I. W. Davies, D. I. C. Scopes, T. Gallagher, Synlett 1993, 85.
36. For the Pd(0)-catalyzed coupling-cyclization reaction of γ-allenic amides with aryl or vinyl halides, see: a) S.-K. Kang, K.-J. Kim, Org. Lett. 2001, 3, 511; I. W. Davies, D. I. C. Scopes, T. Gallagher, Synlett 1993, 85.
37. +-catalyzed cycloisomerization of γ-allenic amides see: a) I. W. Davies, T. Gallagher, R. B. Lamont, D. I. C. Scopes, J. Chem. Soc. Chem. Commun. 1992, 335; b) D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Chem. Soc. Chem. Commun. 1989, 1073; c) R. Kinsman, D. Lathbury, P. Vernon, T. Gallagher, J. Chem. Soc. Chem. Commun. 1987, 243; for lanthanide-catalyzed cycloisomerization of γ-allenic amides, see: V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 121, 3633.
38. +-catalyzed cycloisomerization of γ-allenic amides see: a) I. W. Davies, T. Gallagher, R. B. Lamont, D. I. C. Scopes, J. Chem. Soc. Chem. Commun. 1992, 335; b) D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Chem. Soc. Chem. Commun. 1989, 1073; c) R. Kinsman, D. Lathbury, P. Vernon, T. Gallagher, J. Chem. Soc. Chem. Commun. 1987, 243; for lanthanide-catalyzed cycloisomerization of γ-allenic amides, see: V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 121, 3633.
39. +-catalyzed cycloisomerization of γ-allenic amides see: a) I. W. Davies, T. Gallagher, R. B. Lamont, D. I. C. Scopes, J. Chem. Soc. Chem. Commun. 1992, 335; b) D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Chem. Soc. Chem. Commun. 1989, 1073; c) R. Kinsman, D. Lathbury, P. Vernon, T. Gallagher, J. Chem. Soc. Chem. Commun. 1987, 243; for lanthanide-catalyzed cycloisomerization of γ-allenic amides, see: V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 121, 3633.
40. +-catalyzed cycloisomerization of γ-allenic amides see: a) I. W. Davies, T. Gallagher, R. B. Lamont, D. I. C. Scopes, J. Chem. Soc. Chem. Commun. 1992, 335; b) D. N. A. Fox, D. Lathbury, M. F. Mahon, K. C. Molloy, T. Gallagher, J. Chem. Soc. Chem. Commun. 1989, 1073; c) R. Kinsman, D. Lathbury, P. Vernon, T. Gallagher, J. Chem. Soc. Chem. Commun. 1987, 243; for lanthanide-catalyzed cycloisomerization of γ-allenic amides, see: V. M. Arredondo, S. Tian, F. E. McDonald, T. J. Marks, J. Am. Chem. Soc. 1999, 121, 3633.
41. For the Pd-catalyzed two-component reaction of 2-(2,3-allenyl)malonates with electron-deficient alkenes leading to five-membered carbocycles, see: M. Meguro, Y. Yamamoto, J. Org. Chem. 1999, 64, 694.
42. For the Pd-catalyzed cycloisomerization of allenes with a nucleophilic center, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453; c) B. M. Trost, P.-Y. Michellys, V. J. Gerusz, Angew. Chem. 1997, 109, 1837; Angew. Chem. Int. Ed. 1997, 36, 1750.
43. For the Pd-catalyzed cycloisomerization of allenes with a nucleophilic center, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453; c) B. M. Trost, P.-Y. Michellys, V. J. Gerusz, Angew. Chem. 1997, 109, 1837; Angew. Chem. Int. Ed. 1997, 36, 1750.
44. For the Pd-catalyzed cycloisomerization of allenes with a nucleophilic center, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453; c) B. M. Trost, P.-Y. Michellys, V. J. Gerusz, Angew. Chem. 1997, 109, 1837; Angew. Chem. Int. Ed. 1997, 36, 1750.
45. For the Pd-catalyzed cycloisomerization of allenes with a nucleophilic center, see: a) S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 1747; b) M. Meguro, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 1996, 37, 7453; c) B. M. Trost, P.-Y. Michellys, V. J. Gerusz, Angew. Chem. 1997, 109, 1837; Angew. Chem. Int. Ed. 1997, 36, 1750.
46. For the Pd-catalyzed coupling cyclization of 2-(2,3-allenyl)malonates with organohalides, see: a) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 35, 2881; b) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1985, 26, 3795; c) S. Ma, S. Zhao, Org. Lett. 2000, 2, 2495; d) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837.
47. For the Pd-catalyzed coupling cyclization of 2-(2,3-allenyl)malonates with organohalides, see: a) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 35, 2881; b) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1985, 26, 3795; c) S. Ma, S. Zhao, Org. Lett. 2000, 2, 2495; d) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837.
48. For the Pd-catalyzed coupling cyclization of 2-(2,3-allenyl)malonates with organohalides, see: a) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 35, 2881; b) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1985, 26, 3795; c) S. Ma, S. Zhao, Org. Lett. 2000, 2, 2495; d) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837.
49. For the Pd-catalyzed coupling cyclization of 2-(2,3-allenyl)malonates with organohalides, see: a) L. Besson, J. Bazin, J. Gore, B. Cazes, Tetrahedron Lett. 1994, 35, 2881; b) M. Ahmar, B. Cazes, J. Gore, Tetrahedron Lett. 1985, 26, 3795; c) S. Ma, S. Zhao, Org. Lett. 2000, 2, 2495; d) S. Ma, N. Jiao, S. Zhao, H. Hou, J. Org. Chem. 2002, 67, 2837.
50. int = 0.022. CCDC-189277 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam. ac.uk).