Dimethylzinc-mediated additions of alkenylzirconocenes to aldimines. New methodologies for allylic amine and C-cyclopropylalkylamine syntheses

Journal of the American Chemical Society

Volumn 125, Issue 3, 2003, Pages 761-768

  Wipf, Peter ^a   Kendall, Christopher ^a   Stephenson, Corey R J ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROZIRCONATION;

CHEMICAL BONDS; SYNTHESIS (CHEMICAL); ZINC;

AMINES;

ALDIMINE DERIVATIVE; ALKENYL GROUP; ALLYL COMPOUND; AMINE; CARBON; CYCLOPROPANE DERIVATIVE; IMINE; UNCLASSIFIED DRUG; ZINC DERIVATIVE; ZIRCONOCENE;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOPROPANATION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037460171     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028092a     Document Type: Article

References (84)

1. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49.
2. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
3. (c) Pu, L.; Yu, H.-B. Chem. Rev. 2001, 101, 757.
4. (d) Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. E. Org. React. 2001, 58, 417.
5. (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
6. (b) Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895.
7. (c) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999.
8. Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097.
9. (a) Suzuki, T.; Shibata, T.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1997, 2757.
10. (b) Sato, I.; Kodaka, R.; Shibata, T.; Hirokawa, Y.; Shirai, N.; Ohtake, K.; Soai, K. Tetrahedron: Asymmetry 2000, 11, 2271.
11. (c) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364.
12. (d) Pinho, P.; Andersson, P. Tetrahedron 2001, 57, 1615.
13. (e) Jimeno, C.; Reddy, K. S.; Solà, L.; Moyano, A.; Pericàs, M. A.; Riera, A. Org. Lett. 2000, 2, 3157
14. Katritzky, A. R.; Harris, P. Tetrahedron: Asymmetry 1992, 3, 437.
15. Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53.
16. (a) Hou, X. L.; Zheng, X. L.; Dai, L. X. Tetrahedron Lett. 1998, 39, 6949.
17. (b) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984.
18. Fujihara, H.; Nagai, K.; Tomioka, K. J. Am. Chem. Soc. 2000, 122, 12055.
19. Alvaro, G.; Pacioni, P.; Savoia, D. Chem. Eur. J. 1997, 3, 726.
20. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 1999, 121, 11245.
21. (a) Wipf, P.; Xu, W. Tetrahedron Lett. 1994, 35, 5197.
22. (b) Wipf, P.; Xu, W. Org. Synth. 1996, 74, 205.
23. Wipf, P.; Ribe, S. J. Org. Chem. 1998, 63, 6454.
24. (a) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521.
25. (b) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
26. Wipf, P.; Kendall, C. Chem. Eur. J. 2002, 8, 1778.
27. For related preparations of allylic amines, see: (a) Buchwald, S. L.; Watson, B. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486. (b) Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321. (c) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (d) Pandya, S. U.; Garçon, C.; Chavant, P. Y.; Py, S.; Vallée, Y. J. Chem. Soc., Chem. Commun. 2001, 1806.
28. For related preparations of allylic amines, see: (a) Buchwald, S. L.; Watson, B. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486. (b) Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321. (c) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (d) Pandya, S. U.; Garçon, C.; Chavant, P. Y.; Py, S.; Vallée, Y. J. Chem. Soc., Chem. Commun. 2001, 1806.
29. For related preparations of allylic amines, see: (a) Buchwald, S. L.; Watson, B. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486. (b) Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321. (c) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (d) Pandya, S. U.; Garçon, C.; Chavant, P. Y.; Py, S.; Vallée, Y. J. Chem. Soc., Chem. Commun. 2001, 1806.
30. For related preparations of allylic amines, see: (a) Buchwald, S. L.; Watson, B. T.; Wannamaker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486. (b) Grossman, R. B.; Davis, W. M.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 2321. (c) Hauske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. (d) Pandya, S. U.; Garçon, C.; Chavant, P. Y.; Py, S.; Vallée, Y. J. Chem. Soc., Chem. Commun. 2001, 1806.
31. Wipf, P.; Kendall, C. Org. Lett. 2001, 3, 2773.
32. For a preliminary communication of this work, see: Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122.
33. Soai, K.; Suzuki, T.; Shono, T. J. Chem. Soc., Chem. Commun. 1994, 317.
34. Wipf, P.; Takahashi, H.; Zhuang, N. Pure Appl. Chem. 1998, 70, 1077.
35. Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639.
36. Yamada, K.; Harwood, S. J.; Groger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
37. Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75.
38. 2 is generally considered unreactive in a wide range of modifications of this method: (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256. (b) LeGoff, E. J. Org. Chem. 1964, 29, 2048. (c) Maeda, T.; Tada, H.; Yasuda, K.; Okawara, R. J. Organomet. Chem. 1971, 27, 13. (d) Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973. 46, 892. (e) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1. It has, however, been reported that a mixture of alkene and methylene chloride reacts with heated zinc film at low pressure to give traces of cyclopropane products: (f) Fauveau, C.; Gault, Y.; Gault, F. G. Tetrahedron Lett. 1967, 3149.
39. 2 is generally considered unreactive in a wide range of modifications of this method: (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256. (b) LeGoff, E. J. Org. Chem. 1964, 29, 2048. (c) Maeda, T.; Tada, H.; Yasuda, K.; Okawara, R. J. Organomet. Chem. 1971, 27, 13. (d) Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973. 46, 892. (e) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1. It has, however, been reported that a mixture of alkene and methylene chloride reacts with heated zinc film at low pressure to give traces of cyclopropane products: (f) Fauveau, C.; Gault, Y.; Gault, F. G. Tetrahedron Lett. 1967, 3149.
40. 2 is generally considered unreactive in a wide range of modifications of this method: (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256. (b) LeGoff, E. J. Org. Chem. 1964, 29, 2048. (c) Maeda, T.; Tada, H.; Yasuda, K.; Okawara, R. J. Organomet. Chem. 1971, 27, 13. (d) Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973. 46, 892. (e) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1. It has, however, been reported that a mixture of alkene and methylene chloride reacts with heated zinc film at low pressure to give traces of cyclopropane products: (f) Fauveau, C.; Gault, Y.; Gault, F. G. Tetrahedron Lett. 1967, 3149.
41. 2 is generally considered unreactive in a wide range of modifications of this method: (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256. (b) LeGoff, E. J. Org. Chem. 1964, 29, 2048. (c) Maeda, T.; Tada, H.; Yasuda, K.; Okawara, R. J. Organomet. Chem. 1971, 27, 13. (d) Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973. 46, 892. (e) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1. It has, however, been reported that a mixture of alkene and methylene chloride reacts with heated zinc film at low pressure to give traces of cyclopropane products: (f) Fauveau, C.; Gault, Y.; Gault, F. G. Tetrahedron Lett. 1967, 3149.
42. 2 is generally considered unreactive in a wide range of modifications of this method: (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256. (b) LeGoff, E. J. Org. Chem. 1964, 29, 2048. (c) Maeda, T.; Tada, H.; Yasuda, K.; Okawara, R. J. Organomet. Chem. 1971, 27, 13. (d) Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973. 46, 892. (e) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1. It has, however, been reported that a mixture of alkene and methylene chloride reacts with heated zinc film at low pressure to give traces of cyclopropane products: (f) Fauveau, C.; Gault, Y.; Gault, F. G. Tetrahedron Lett. 1967, 3149.
43. 2 is generally considered unreactive in a wide range of modifications of this method: (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256. (b) LeGoff, E. J. Org. Chem. 1964, 29, 2048. (c) Maeda, T.; Tada, H.; Yasuda, K.; Okawara, R. J. Organomet. Chem. 1971, 27, 13. (d) Miyano, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1973. 46, 892. (e) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1. It has, however, been reported that a mixture of alkene and methylene chloride reacts with heated zinc film at low pressure to give traces of cyclopropane products: (f) Fauveau, C.; Gault, Y.; Gault, F. G. Tetrahedron Lett. 1967, 3149.
44. Charette, A. B.; Wilb, N. Synlett 2002, 176.
45. Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357.
46. (a) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
47. (b) Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 2592.
48. Compound syn-10 was expected to be the major diastereomer based upon extensive precedence by, among others: (a) Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966. (b) Harada, S.; Kowase, N.; Tabuchi, N.; Taguchi, T.; Dobashi, Y,; Dobashi, A.; Hanzawa, Y. Tetrahedron 1998, 54, 753.
49. Compound syn-10 was expected to be the major diastereomer based upon extensive precedence by, among others: (a) Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966. (b) Harada, S.; Kowase, N.; Tabuchi, N.; Taguchi, T.; Dobashi, Y,; Dobashi, A.; Hanzawa, Y. Tetrahedron 1998, 54, 753.
50. Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 18, 1977.
51. N2 product, anti-11, was confirmed by subjecting anti-10 to analogous Mitsunobu reaction conditions. A 15:85 mixture of diastereomers favoring the epimer, syn-11, was isolated in the latter conversion.
52. The reduced cyclopropanation rate for the distal double bond can readily be explained by the greater distance between the N-ligated zinc carbenoid specied and the alkene in the transition-state structures (cf. Scheme 9). Due to the long N-Zn and Zn-C bonds (ca. 2 Å), intramolecular delivery is still feasible, however.
53. Negishi, E.; Takahashi, T. Synthesis 1988, 1.
54. Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P, J., Eds.; Wiley-VCH: New York, 1998; pp 203-229.
55. Bick, S.; Zimmermann, S.; Meuer, H.; Sheldrick, W. S.; Welzel, P. Tetrahedron 1993, 49, 2457.
56. (a) Wipf, P.; Lim, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1068.
57. (b) Ribe, S.; Wipf, P. J. Chem. Soc., Chem. Commun. 2001, 299.
58. Iwasawa, N.; Maeyama, K. J. Org. Chem. 1997, 62, 1918.
59. (a) Faust, R. Angew. Chem., Int. Ed. 2001, 40, 2251.
60. (b) Donaldson, W. A. Tetrahedron 2001, 57, 8589.
61. (c) Barrett, A. G. M.; Tuestin, G. J. J. Chem. Soc., Chem. Commun. 1995, 355.
62. Yachi, K.; Shinokubo, H,; Oshima, K. Angew. Chem., Int. Ed, 1998, 37, 2515.
63. See Scheme 5 and refs 23e and 27, as well as: Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525.
64. Zeng, F.; Negishi, E. Org. Lett. 2001, 3, 719.
65. Srebnick, M. Tetrahedron Lett. 1991, 32, 2449.
66. (a) Russ, P.; Ezzitouni, A.; Marquez, V. E. Tetrahedron Lett. 1997, 38, 723.
67. (b) Momose, T.; Nishio, T.; Kirihara, M. Tetrahedron Lett. 2002, 37, 4987.
68. Charette, A. B.; Beauchemin, A.; Francoeur, S. J. Am. Chem. Soc. 2001, 123, 8139.
69. Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974.
70. (a) Charette, A. B.; Beauchemin, A.; Francoeur, S.; Bélanger-Gariépy, F.; Enright, G. D. Chem. Commun. 2002, 466.
71. (b) Charette, A. B.; Francoeur, S.; Martel, J.; Wilb, N. Angew. Chem., Int. Ed. 2000, 39, 4539.
72. (c) Yang, Z. Q.; Lorenz, J. C.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621.
73. (a) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1998, 120, 5844.
74. (b) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013.
75. (c) Charette, A. B.; Brochu, C. J. Am. Chem. Soc. 1995, 117, 11367.
76. (d) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12160.
77. For discussions of the transition-state geometry of Simmons-Smith cyclopropanations, see: (a) Bernardi, F.; Bottoni, A.; Miscione, G. P. J. Am. Chem. Soc. 1997, 119, 12300. (b) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
78. For discussions of the transition-state geometry of Simmons-Smith cyclopropanations, see: (a) Bernardi, F.; Bottoni, A.; Miscione, G. P. J. Am. Chem. Soc. 1997, 119, 12300. (b) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
79. Charette, A. B.; Lebel, H.; Gagnon, A. Tetrahedron 1999, 55, 8845.
80. Tietze, L. F. Chem. Rev. 1996, 96, 115.
81. For typical multistep approaches to C-cyclopropylalkylamines, see, for example: (a) Shuto, S.; Ono, S.; Imoto, H.; Yoshii, K.; Matsuda, A. J. Med. Chem. 1998, 41, 3507. (b) Ma, D.; Ma, Z. Tetrahedron Lett. 1997, 38, 7599. (c) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167. For a 3-component synthesis of aliphatic amines, see: (d) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.
82. For typical multistep approaches to C-cyclopropylalkylamines, see, for example: (a) Shuto, S.; Ono, S.; Imoto, H.; Yoshii, K.; Matsuda, A. J. Med. Chem. 1998, 41, 3507. (b) Ma, D.; Ma, Z. Tetrahedron Lett. 1997, 38, 7599. (c) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167. For a 3-component synthesis of aliphatic amines, see: (d) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.
83. For typical multistep approaches to C-cyclopropylalkylamines, see, for example: (a) Shuto, S.; Ono, S.; Imoto, H.; Yoshii, K.; Matsuda, A. J. Med. Chem. 1998, 41, 3507. (b) Ma, D.; Ma, Z. Tetrahedron Lett. 1997, 38, 7599. (c) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167. For a 3-component synthesis of aliphatic amines, see: (d) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.
84. For typical multistep approaches to C-cyclopropylalkylamines, see, for example: (a) Shuto, S.; Ono, S.; Imoto, H.; Yoshii, K.; Matsuda, A. J. Med. Chem. 1998, 41, 3507. (b) Ma, D.; Ma, Z. Tetrahedron Lett. 1997, 38, 7599. (c) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167. For a 3-component synthesis of aliphatic amines, see: (d) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409.