Cycloadditions of nonstabilized 2-azaallyllithiums (2-azaallyl anions) and azomethine ylides with alkenes: [3+2] Approaches to pyrrolidines and application to alkaloid total synthesis

Synlett

Volumn , Issue 7, 2003, Pages 903-921

  Pearson, William H ^a,b   Stoy, Patrick ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b Berry and Associates Inc   (United States)

Author keywords

Alkaloid synthesis; Anionic cycloaddition; Heterocycles; Organolithium; Tin lithium exchange

Indexed keywords

ALKALOID DERIVATIVE; ALKENE DERIVATIVE; ALKYL GROUP; ALLYL COMPOUND; AZOMETHINE YLIDE; ESTER DERIVATIVE; HYDROGEN; LITHIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLOADDITION; ENANTIOSELECTIVITY; LOW TEMPERATURE; METHODOLOGY; MOLECULAR DYNAMICS; MOLECULAR STABILITY; POLYMERIZATION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038576749     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (80)

1. Ingold, C. K.; Shoppee, C. W. J. Chem. Soc. 1929, 1199.
2. Hauser, C. R.; Flur, I. C.; Kantor, S. W. J. Am. Chem. Soc. 1949, 71, 294.
3. (a) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1974, 13, 627.
4. (b) Kauffmann, T.; Berg, H.; Köppelmann, E. Angew. Chem., Int. Ed. Engl. 1970, 9, 380.
5. Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Bull. Chem. Soc. Jpn. 1986, 59, 2537.
6. Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Chem. Lett. 1984, 801.
7. Achiwa, K.; Imai, N.; Motoyama, T.; Sekiya, M. Chem. Lett. 1984, 2041.
8. Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646.
9. Tsuge, O.; Kanemasa, S.; Yamada, T.; Matsuda, K. J. Org. Chem. 1987, 52, 2523.
10. Dehnel, A.; Lavielle, G. Tetrahedron Lett. 1980, 21, 1315.
11. Houwing, H. A.; van Leusen, A. M. J. Heterocycl. Chem. 1981, 18, 1127.
12. Fouchet, B.; Joucla, M.; Hamelin, J. Tetrahedron Lett. 1981, 22, 3397.
13. Grigg, R.; Sridharan, V. In Advances in Cycloaddition, Vol. 3; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1993, 161-204.
14. Kanemasa, S.; Tsuge, O. In Advances in Cycloaddition, Vol. 3; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1993, 99-159.
15. Kanemasa, S. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; John Wiley & Sons: New York, 2002, 755-815.
16. Harwood, L. M.; Vickers, R. J. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; John Wiley & Sons: New York, 2002, 169-252.
17. Grigg, R.; Kemp, J. Tetrahedron Lett. 1978, 2823.
18. Kanemasa, S.; Yamamoto, H.; Wada, E.; Sakurai, T.; Urushido, K. Bull. Chem. Soc. Jpn. 1990, 63, 2857.
19. Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27, 981.
20. Tsuge, O.; Kanemasa, S.; Matsuda, K. Chem. Lett. 1984, 1827.
21. Pearson, W. H.; Walters, M. A.; Oswell, K. D. J. Am. Chem. Soc. 1986, 108, 2769.
22. A single report of the use of an unactivated alkene in a cycloaddition with a 2-azaallyl anion preceded this work wherein Kauffmann's 1,3-diphenyl-2-azaallyllithium was used to capture ethylene that was generated by the basepromoted decomposition of THF, see: Kamata, K.; Terashima, M. Heterocycles 1980, 14, 205.
23. Pearson, W. H.; Walters, M. A.; Harter, W. G. In Electronic Conference on Trends in Heterocyclic Chemistry; Royal Society of Chemistry: Cambridge UK, 1996, Paper No. 60; http://www.ch.ic.ac.uk/ectoc/echet96/papers/060/index.htm.
24. Pearson, W. H.; Walters, M. A.; Rosen, M. K.; Harter, W. G. Arkivoc 2002, in press.
25. Kauffmann, T.; Habersaat, K.; Köppelmann, E. Angew. Chem., Int. Ed. Engl. 1972, 11, 291.
26. Wiberg, K. B.; Breneman, C. M.; LePage, T. J. J. Am. Chem. Soc. 1990, 112, 61.
27. Pearson, W. H.; Szura, D. P.; Harter, W. G. Tetrahedron Lett. 1988, 29, 761.
28. Pearson, W. H.; Szura, D. P.; Postich, M. J. J. Am. Chem. Soc. 1992, 114, 1329.
29. Pearson, W. H.; Postich, M. J. J. Org. Chem. 1992, 57, 6354.
30. Chong, J. M.; Park, S. B. J. Org. Chem. 1992, 57, 2220.
31. Pearson, W. H.; Ren, Y. J. Org. Chem. 1999, 64, 688.
32. Kauffmann, T.; Ahlers, H.; Hamsen, A.; Schulz, H.; Tilhard, H.-J.; Vahrenhorst, A. Angew. Chem., Int. Ed. Engl. 1977, 16, 119.
33. Pearson, W. H.; Mi, Y. Tetrahedron Lett. 1997, 38, 5441.
34. Pearson, W. H.; Jacobs, V. A. Tetrahedron Lett. 1994, 35, 001.
35. Pearson, W. H.; Stevens, E. P. Tetrahedron Lett. 1994, 35, 2641.
36. Pearson, W. H.; Stevens, E. P. J. Org. Chem. 1998, 63, 9812.
37. Pearson, W. H.; Stevens, E. P.; Aponick, A. Tetrahedron Lett. 2001, 42, 7361.
38. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669.
39. Pearson, W. H.; Mi, Y.; Lee, I. Y.; Stoy, P. J. Am. Chem. Soc. 2001, 123, 6724.
40. Clark, R. B.; Pearson, W. H. Org. Lett. 1999, 1, 349.
41. Carbolithiation reviews: (a) Knochel, P. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms, Vol. 3; Coxon, J. M., Ed.; JAI Press: Greenwich CT, 1994, 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535.
42. Carbolithiation reviews: (a) Knochel, P. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms, Vol. 3; Coxon, J. M., Ed.; JAI Press: Greenwich CT, 1994, 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535.
43. Carbolithiation reviews: (a) Knochel, P. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms, Vol. 3; Coxon, J. M., Ed.; JAI Press: Greenwich CT, 1994, 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535.
44. For lithium-ene reactions of allylic organolithiums with alkenes see the following references and the earlier work cited therein: (a) Dieters, A.; Hoppe, D. Angew. Chem. Int. Ed. 1999, 38, 546. (b) Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241. (c) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412.
45. For lithium-ene reactions of allylic organolithiums with alkenes see the following references and the earlier work cited therein: (a) Dieters, A.; Hoppe, D. Angew. Chem. Int. Ed. 1999, 38, 546. (b) Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241. (c) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412.
46. For lithium-ene reactions of allylic organolithiums with alkenes see the following references and the earlier work cited therein: (a) Dieters, A.; Hoppe, D. Angew. Chem. Int. Ed. 1999, 38, 546. (b) Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241. (c) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412.
47. Sauers, R. R. Tetrahedron Lett. 1996, 37, 7679.
48. Neumann, F.; Lambert, C.; Schleyer, P. V. R. J. Am. Chem. Soc. 1998, 120, 3357.
49. Kauffmann, T.; Köppelmann, E. Angew. Chem., Int. Ed. Engl. 1972, 11, 290.
50. For a structure proof of one of Kauffmann' s cycloaddition products see: Ivanov, P. M.; Mikhova, B. P.; Spassov, S. L. J. Mol. Struct. 1996, 377, 19.
51. Pearson, W. H.; Barta, N. S.; Kampf, J. W. Tetrahedron Lett. 1997, 38, 3369.
52. Pearson, W. H.; Mans, D. M.; Kampf, J. W. Org. Lett. 2002, 4, 3099.
53. For a brief study on the cycloaddition of Kauffmann's 1,3-diphenyl-2-azaallyllithium with cycloheptatriene see: Bower, D. J.; Howden, M. E. H. J. Chem. Soc., Perkin Trans. 1 1980, 672.
54. (a) Vedejs, E.; West, F. G. Chem. Rev. 1986, 86, 941.
55. (b) Vedejs, E. In Advances in Cycloaddition, Vol. 1; Curran, D. P., Ed.; JAI Press: Greenwich CT, 1988, 33-51.
56. (c) Tominaga, Y.; Hojo, M.; Hosomi, A. Yuki Gosei Kagaku Kyokaishi 1992, 50, 48.
57. Other routes to nonstabilized azomethine ylides include decarboxylative methods and the deprotonation of tertiary amine N-oxides. For leading references see: (a) Tsuge, O.; Kanemasa, S.; Ohe, M.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 4079. (b) Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1988, 44, 4953. (c) Chastanet, J.; Roussi, G. J. Org. Chem. 1988, 53, 3808.
58. Other routes to nonstabilized azomethine ylides include decarboxylative methods and the deprotonation of tertiary amine N-oxides. For leading references see: (a) Tsuge, O.; Kanemasa, S.; Ohe, M.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 4079. (b) Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1988, 44, 4953. (c) Chastanet, J.; Roussi, G. J. Org. Chem. 1988, 53, 3808.
59. Other routes to nonstabilized azomethine ylides include decarboxylative methods and the deprotonation of tertiary amine N-oxides. For leading references see: (a) Tsuge, O.; Kanemasa, S.; Ohe, M.; Takenaka, S. Bull. Chem. Soc. Jpn. 1987, 60, 4079. (b) Ardill, H.; Grigg, R.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1988, 44, 4953. (c) Chastanet, J.; Roussi, G. J. Org. Chem. 1988, 53, 3808.
60. (a) Achiwa, K.; Imai, N.; Inaoka, T.; Sekiya, M. Chem. Pharm. Bull. 1984, 32, 2878.
61. (b) Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987; 35, 593.
62. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1999, 40, 4467.
63. Pearson, W. H.; Aponick, A. Organic Lett. 2001, 3, 1327.
64. Pearson, W. H.; Lovering, F. E. J. Am. Chem. Soc. 1995, 117, 12336.
65. Pearson, W. H.; Lovering, F. E. J. Org. Chem. 1998, 63, 3607.
66. Pearson, W. H.; Lian, B. W. Angew. Chem., Int. Ed. Engl. 1998, 37, 1724.
67. Pearson, W. H.; Lovering, F. E. Tetrahedron Lett. 1994, 35, 9173.
68. Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662.
69. Martin, S. F.; Davidsen, S. K.; Puckette, T. A. J. Org. Chem. 1987, 52, 1962.
70. Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691.
71. Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686.
72. Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865.
73. Sun, P.; Sun, C.; Weinreb, S. M. Org. Lett. 2001, 3, 3507.
74. Sun, P.; Sun, C.; Weinreb, S. M. J. Org. Chem. 2002, 67, 4337.
75. Abe, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 2000, 41, 1205.
76. Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2000, 122, 4583.
77. Lepadiformine has also been synthesized by Greshock and Funk: Greshock, T. J.; Funk, R. L. Org. Lett. 2001, 3, 3511.
78. Marshall, J. A.; Garofalo, A. W. J. Org. Chem. 1993, 58, 3675.
79. Ardakani, M. A.; Smalley, R. K. Tetrahedron Lett. 1979, 4769.
80. Azadi-Ardakani, M.; Alkhader, M. A.; Lippiatt, J. H.; Patel, D. I.; Smalley, R. K.; Higson, S. J. Chem. Soc., Perkin Trans. 1 1986, 1107.