Studies on Pd(II)-catalyzed coupling-cyclization of α- or β-amino allenes with allylic halides

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 5943-5949

  Ma, Shengming ^a   Yu, Fei ^a   Gao, Wenzhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING-CYCLIZATION;

HALOGEN COMPOUNDS; PALLADIUM; X RAY DIFFRACTION ANALYSIS;

CATALYST ACTIVITY;

3 PIPERIDEINE DERIVATIVE; ALLENE DERIVATIVE; ALLYL COMPOUND; HALIDE; PALLADIUM; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MATERIALS; ORGANIC CHEMISTRY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 0038373078     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0342469     Document Type: Article

References (70)

1. (a) Zimmer, R.; Dinesh, C. U.; Nadanan, E. F.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
2. (b) Hiemstra, H. Curr. Trends Org. Synth. 1998.
3. (c) Reissig, H. U.; Hormuth, S.; Schade, W.; Amombo, M. O.; Watanabe, T.; Pulz, R.; Hausherr, A.; Zimmer, R. J. Heterocycl. Chem. 2000, 37, 597.
4. (d) Reissig, H, U.; Schade, W.; Amombo, M. O.; Watanabe, T.; Pulz, R.; Hausherr, A. A. Pure Appl. Chem. 2002, 74, 175.
5. (e) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 112, 3590.
6. (a) Olsson, L. I.; Claesson, A. Synthesis 1979, 743.
7. (b) Nikam, S. S.; Chu, K. H.; Wang, K. K. J. Org. Chem. 1986, 51, 745.
8. (c) Gelin, R.; Gelin, S.; Albrand, M. Bull. Soc. Chim. Fr. 1972, 1946.
9. (d) Bridges, A. J.; Thomas, R. D. J. Chem. Soc. Chem. Commun. 1984, 694.
10. (e) Chilot, J.-J.; Doutheau, A.; Gore, J. Tetrahedron Lett. 1982, 23, 4693.
11. (f) Chilot, J.-J.; Doutheau, A.; Gore, J. Bull. Soc. Chim. Fr. 1984, II-307.
12. (a) Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324.
13. (b) Kang, S.-K.; Yamaguchi, T.; Pyun, S.-J.; Lee, Y.-T.; Baik, T.-G. Tetrahedron Lett. 1998, 39, 2127.
14. (c) Walkup, R. D.; Guan, L.; Kim, Y. S.; Kim, S. W. Tetrahedron Lett. 1995, 36, 3805.
15. (d) Walkup, R. D.; Guan, L.; Mosher, M. D.; Kim, Y. S.; Kim, S. W. Synlett 1993, 88.
16. (a) Hashmi, A. S. K.; Rupert, T. L.; Knoefel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295.
17. (b) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. Angew. Chem., Int. Ed. 2000, 39, 2285.
18. (c) Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 960.
19. (d) Marshall, J. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796.
20. (e) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
21. (f) Jonasson, C.; Horvath, A.; Backvall, J.-E. J. Am. Chem. Soc. 2000, 122, 9600.
22. (a) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441.
23. (b) Trost, B. M.; Prinkerton, A. B. J. Am. Chem. Soc. 1999, 121, 10842.
24. (a) Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 4257.
25. (b) Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1992, 57, 6377.
26. (c) Kimura, M.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 3764.
27. (d) Karstens, W. F. J.; Klomp, D.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron 2001, 57, 5123.
28. (a) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904.
29. (b) Kang, S.-K.; Kim, K.-J. Org. Lett. 2001, 3, 511.
30. (c) Anzai, M.; Toda, A.; Ohno, H.; Takemoto, Y.; Fuji, N.; Ibuka, T. Tetrahedron Lett. 1999, 40, 7393.
31. (d) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717.
32. (e) Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Yamaoka, Y.; Fuji, N.; Ibuka, T. J Org. Chem. 1999, 64, 2992.
33. (f) Karstens, W. F. J.; Stol, M.; Rutjes, F. P. J. T.; Hiemstra, H. Synlett 1998, 1126.
34. (g) Karstens, W. F. J.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron Lett. 1997, 38, 6275.
35. (h) Davies, I. W.; Scopes, D. I. C.; Gallagher, T. Synlett 1993, 85.
36. (a) Amombo, M. O.; Hausherr, A.; Reissig, H.-U. Synlett 1999, 1871.
37. (b) Davies, I. W.; Gallagher. T.; Lamont, R. B.; Scopes, D. I. C. J. Chem. Soc., Chem. Commun. 1992, 335.
38. (c) Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1989, 1073.
39. (d) Prasad, J. S.; Liebeskind, L. S. Tetrahedron Lett. 1988, 29, 4253.
40. (e) Kinsman, R.; Lathbury, D.; Vernon, P.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1987, 243.
41. For a review on carbopalladation reaction of allenes, see: Ma, S. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Eds.; John Wiley & Sons: New York, 2002.
42. For the corresponding reaction of 1,2-allenyl ketones with organic halides to afford furans, see: (a) Ma, S.; Zhang, J. Chem. Commun. 2000, 117. (b) Ma. S.; Li, L. Org. Lett. 2000, 2, 941.
43. For the corresponding reaction of 1,2-allenyl ketones with organic halides to afford furans, see: (a) Ma, S.; Zhang, J. Chem. Commun. 2000, 117. (b) Ma. S.; Li, L. Org. Lett. 2000, 2, 941.
44. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
45. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
46. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
47. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
48. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
49. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
50. For the transition-metal-catalyzed or -mediated cyclization of 1,2-allenyl carboxylic acids to afford β-substituted butenolides, see: (a) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387. (b) Ma, S.; Duan, D.; Shi, Z. Org. Lett. 2000, 2, 1491. (c) Ma, S.; Wu, S. J. Org. Chem. 1999, 64, 9314; (d) Ma, S.; Shi, Z.; Wu, S. Tetrahedron: Asymmetry 2001, 12, 193. (d) Ma, S.; Yu, Z. Angew. Chem. Int. Ed. 2002, 114, 1775. (e) Ma, S.; Shi, Z. Chem. Commun. 2002, 540. (f) Ma, S.; Wu, S. Chem. Commun. 2001, 441.
51. For the corresponding Pd(0)-catalyzed coupling-cyclization of 2,3-allenols with organic halides to afford vinylic oxiranes, see: Ma, S.; Zhao, S. J. Am. Chem. Soc. 1999, 121, 7943 and ref 3c.
52. (a) Ma, S.; Gao, W. Tetrahedron Lett. 2000, 41, 8933.
53. (b) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104.
54. (a) Brandsma, L., Ed. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988.
55. (b) Ma, S.; Jiao, N.; Zhao, S.; Hou, H. J. Org. Chem. 2002, 67, 2837.
56. Kazmaier, U.; Gorbitz, C. H. Synthesis 1996, 1489.
57. Roush, W. R.; Straud, J. A.; Brown, R. T. J. Org. Chem. 1987, 52, 5127.
58. (a) Tatsuno, Y.; Yoshida, T.; Otsuka, S. Inorg. Synth. 1989, 28, 342.
59. (b) Sakakibara, M.; Takahashi, Y.; Sakai, S.; Ishii, Y. Chem. Comunm. 1969, 396.
60. Recently, Hiemstra et al. reported their results on the coupling-cyclization of allenes containing lactam and oxazolidinone moiety. The author proposed a Pd(0)-catalyzed pathway because of the experimental fact that a stoichiometric amount of π-allyl palladium chloride dimer could successfully promote the reaction to afford the products in moderate yield; see ref 6d.
61. 3 afforded 15 in 96% yield.
62. Redemann, C. D.; Rice, F. O.; Roberts, R.; Ward, H. P. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 244.
63. int = 0.0477), no observation [I > 2σ] 2996, parameters 297.
64. int = 0.0948), no observation [I > 2σ] 2121, parameters 305.
65. Xu, D. W.; Li, Z, Y.; Ma, S. M. Tetrahedron Lett., in press.
66. (a) Marshall, J. A.; Robinson, E. D.; Zapata, A. J. Org. Chem. 1989, 54, 4, 5854.
67. (b) Marshall, J. A.; Wang, X. J. Org. Chem. 1991, 56, 4913.
68. (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1990, 112, 7434;
69. (b) Witulski, B.; Zimmermann, A. Synlett 2002, 11, 1855.
70. The absolute configurations of (S)-7m and (R)-7n were tentatively assigned based on the stereochemical outcome of oxymetalation of optically active 2,3-allenoic acids, see refs 11e-f.