Reactions of n-arylsulfonyl-2,3-cis- and n-arylsulfonyl-2,3-frans-3-alkyl-2-vinylaziridines with organocopper reagents: importance of 2,3-cis-stereochemistry in controlling regio- and stereoselectivity

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 7053-7061

  Toda, Ayako ^a   Aoyama, Hiroshi ^a   Mimura, Norio ^a   Ohno, Hiroaki ^a   Fujii, Nobutaka ^a   Ibuka, Toshiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001115347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9810157     Document Type: Article

References (126)

1. For reviews of syntheses and reactions of activated and unactivated aziridines, see: Pawda, A.; Woolhouse, A. D. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon: Oxford, 1984; Vol. 7, pp 47-93.
2. Kasai, M.; Kono, M. Synlett 1992, 778.
3. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994,33,599.
4. Osborn, H. M. I.; Sweeney, J. Tetrahedon: Asymmetry 1997,8,1693.
5. Rayner, C. M. Synlett 1997, 11.
6. Ibuka, T. Chem. Soc. Rev. 1998, 27, 145.
7. Stamm, H.; Weiss, R. Synthesis 1986, 392.
8. (a) Stamm, H.; Weiss, R. Synthesis 1986, 395.
9. (b) Brigaud, T.; Laurent, E.; Tardivel, R.; Cebulska, Z.; Bartnik, R. J. Chem. Res., Synop. 1994, 330.
10. Matsumoto, K.; lida, H.; Uchida, T.; Yabe, Y.; Kakehi, A. Chem. Express 1993, 8, 609.
11. Stamm, H.; Assithianakis, P.; Buchholz, B.; Weiss, R. Tetrahedron Lett. 1982, 23, 5021.
12. Howson, W.; Osborn, H. M. I.; Sweeney, J. J. Chem. Soc., Perkin Trans, l 1995, 2439.
13. Oppolzer, W.; Flaskamp, E. Helu. Chim. Ada 1977, 60, 204.
14. (a) Eis, M. J.; Ganem, B. Tetrahedron Lett. 1985, 26, 1153.
15. (b) Duréault, A.; Greek, C.; Depezay, J. C. Tetrahedron Lett. 1986, 27, 4157.
16. Duréault, A.; Tranchepain, I.; Depezay, J.-C. J. Org. Chem. 1989,54,5324.
17. Kozikowski, A. P.; Ishida, H.; Isobe, K. J. Org. Chem. 1979,44,2788.
18. (e) Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151.
19. (f) Tanner, D.; Groth, T. Tetrahedron 1997, 53, 16139.
20. (g) Tanner, D.; Birgersson, C.; Dhaliwal, H. K. Tetrahedron Lett. 1990, 31, 1903.
21. (h) Tanner, D.; Somfai, P. Tetrahedron 1988, 44, 619.
22. Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153.
23. (a) Shigematsu, N.; Setoi, H.; Uchida, I.; Shibata, T.; Terano, H.; Hashimoto, M. Tetrahedron Lett. 1988, 29, 5147.
24. (b) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980,53, 283.
25. Cernerud, M.; Adolfsson, H.; Moberg, C. Tetrahedron: Asymmetry 1997,8, 2655.
26. Maligres, P. E.; See, M. M.; Askin, D.; Reider, P. J. Tetrahedron Lett. 1997, 38, 5253.
27. (a) Tomalia, D. A.; Sheetz, D. P.; Ham, G. E. J. Org. Chem. 1970,35, 47.
28. (b) Nakajima, K.; Oda, H.; Okawa, K. Bull. Chem. Soc. Jpn. 1983,56, 520.
29. Lin, P.-Y.; Bellos, K.; Stamm, H.; Onistschenko, A. Tetrahedron 1992,48, 2359.
30. Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881.
31. (a) Nakajima, K; Neya, M.; Yamada, S.; Okawa, K. Bull. Chem. Soc. Jpn. 1982,55, 3049.
32. (b) Bodenan, J.; Chanet-Ray, J.; Vessicrc, R. Synthesis 1992, 288.
33. For an aziridine ring-opening reaction with acetic acid, see: Atkinson, R. S.; Ayscough, A. P.; Rattrell, W. T.; Raynham, T. M. Tetrahedron Lett. 1998, 39, 4377.
34. (a) Marshall, J. A.; Audia, V. H.; Jenson, T. M.; Guida, W. C. Tetrahedron 1986, 42, 1703.
35. (b) Marshall, J. A.; Audia, V. H. J. Org. Chem. 1987, 52, 1106.
36. Marshall, J. A.; Trometer, J. D. Tetrahedron Lett. 1987, 28, 4985.
37. Marshall, J. A.; Trometer, J. D.; Clearly, D. G. Tetrahedron 1989, 45, 391.
38. (e) Marshall, J. A. Chem. Rev. 1989, 89, 1503.
39. (f) Marshall, J. A.; Blough, B. E. J. Org. Chem. 1990, 55, 1540.
40. (g) Marshall, J. A.; Blough, B. E. J. Org. Chem. 1991, 56, 2225.
41. (h) Marshall, J. A.; Crute, T. D., III.; Hsi, J. D. J. Org. Chem. 1992, 57, 115.
42. Marino, J. P.; Floyd, D. M. Tetrahedron Lett. 1979, 675.
43. Marino, J. P.; Hatanaka, N. J. Org. Chem. 1979, 44, 4467.
44. Marino, J. P.; Abe, H. Synthesis 1980, 872.
45. Marino, J. P.; Abe, H. J. Org. Chem. 1981,46, 5379.
46. Marino, J. P.; Abe, H. J. Am. Chem. Soc. 1981, 103, 2907.
47. Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165.
48. Marino, J. P.; lla, R.; Laborde, E. J. Org. Chem. 1984,49,5279.
49. Marino, J. P.; Fernândez de la Pradilla, R.; Laborde, E. J. Org. Chem. 1987,52, 4898.
50. Fernândez de la Pradilla, R.; Rubio, M. B.; Marino, J. P. Viso, A. Tetrahedron Lett. 1992, 33, 4985.
51. Marino, J. P.; Viso, A.; Fernândez de la Pradilla, R.; Fernândez, P. J. Org. Chem. 1991, 56, 1349.
52. Marino, J. P.; Anna, L. J.; Fernândez de la Pradilla, R.; Martînez, M. V.; Montero, C.; Viso, A. Tetrahedron Lett. 1996, 37, 8031.
53. Cantrill, A. A.; Jarvis, A. N.; Osborn, H. M. L; Ouadi, A.; Sweeney, J. B. Synlett 1996, 847.
54. A preliminary communication of this work has appeared: Aoyama, H.; Mimura, N.; Ohno, H.; Ishii, K; Toda, A.; Tamamura, H.; Otaka, A.; Fujii, N.; Ibuka, T. Tetrahedron Lett. 1997, 38, 7383.
55. (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Fujii, N.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1994,33, 652.
56. (b) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994,59, 4875.
57. Fujii, N.; Nakai, K.; Tamamura, H.; Otaka, A.; Mimura, N.; Miwa, Y.; Taga, T.; Yamamoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans. 1 1995, 1359.
58. Ibuka, T.; Akaji, M.; Mimura, N.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 2849.
59. (e) Ibuka, T.; Mimura, N.; Ohno, H.; Nakai, K.; Akaji, M.; Habashita, H.; Tamamura, H.; Miwa, Y.; Taga, T.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997,62,2982.
60. (f) Wipf, P.; Henninger, T. C. J. Org. Chem. 1997, 62, 1486.
61. Harn, G. E. J. Org. Chem. 1964, 29, 3052.
62. (a) Osborn, H. M. I.; Sweeney, J. B. Synlett 1994,145.
63. (b) Berry, M. B.; Craig, D.; Jones, P. S.; Rowlands, G. J. Chem. Commun. 1997, 2141.
64. Cantrill, A. A.; Osborn, H. M. L; Sweeney, J. Tetrahedron 1998, 54, 2181.
65. Hou, X.-L.; Yang, X.-F.; Dai, L.-X.; Chen, X.-F. Chem. Commun. 1998, 747.
66. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991.
67. Baldwin, J. E.; Spivey, A. C.; Schofield, C. J.; Sweeney, J. B. Tetrahedron 1993, 49, 6309.
68. Vedejs, E.; Lin, S. J. Org. Chem. 1994, 59, 1602.
69. Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999.
70. Craig, D.; McCague, R.; Potter, G. A.; Williams, M. R. V. Synlett 1998, 55 and 58.
71. Ibuka, T.; Nakai, K.; Akaji, M.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron 1996, 52, 11739.
72. McKennon, M. J.; Meyers, A. L; Drauz, K.; Schwärm, M. J. Org. Chem. 1993, 58, 3568.
73. (a) Coutrot, P.; Elgadi, A.; Grison, C. Heterocydes 1989, 28, 1179.
74. (b) Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
75. Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243.
76. Ziegler, F. E.; Belema, M. J. Org. Chem. 1994, 59, 7962.
77. Lipshutz, B. H.; Wilhelm, R. S.; Kozlowski, J. A. Tetrahedron 1984, 40, 5005.
78. Lipshutz, B. H.; Sharma, S.; Ellsworth, E. L. J. Am. Chem. Soc. 1990, 112, 4032.
79. 2·2LiBr has been used throughout this paper as a matter of convenience. We are not concerned about the exact constitution, but watch the reactive species as a reagent system. See also: Lipshutz, B. H. Synthesis 1987, 325.
80. Lipshutz, B. H. In Organometallic in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; p 283.
81. (a) Bertz, S. H. J. Am. Chem. Soc. 1990, 112, 4031.
82. (b) Bertz, S. H.; Miao, G.; Eliksson, M. J. Chem. Soc., Chem. Commun. 1996, 815.
83. Bertz, S. H.; Dabbagh, G.; He, X.; Power, P. P. J. Am. Chem. Soc. 1993, 115, 11640.
84. See also: Stemmler, T.; Penner-Hahn, J. E.; Knöchel, P. J. Am. Chem. Soc. 1993,115, 348.
85. Synder, J. P.; Spangler, D. P.; Behling, J. R.; Rossiter, B. E. J. Org. Chem. 1994, 59, 2665.
86. Similar results were obtained by treatment of (2R,3S)-2,3-cisN,N-diphenylphosphinoyl-3-(l-methylpropyl)-2-vinylaziridine, prepared from (S)-isoleucine, with methylcopper reagents.
87. Dardenne, G.; Casimir, J.; Marlier, M.; Larsen, P. O. Phytochemistry 1974,13,1897.
88. Havlícek, L.; Hanus, J. Collect. Czech. Chem. Commun. 1991, 56, 1365.
89. Fagg, G. E.; Olpe, H. R.; Pozza, M. F.; Baud, J.; Steinmann, M.; Schmutz, M.; Portet, C.; Baumann, P.; Thedinga, K.; Bittiger, H.; Allgeier, H.; Heckendorn, R.; Angst, C.; Brundish, D.; Dingwall, J. G. Br. J. Pharmacol. 1990,99, 791.
90. Ibuka, T.; Suzuki, K.; Habashita, H.; Otaka, A.; Tamamura, H.; Mimura, N.; Miwa, Y.; Taga, T.; Fujii, N. J. Chem. Soc., Chem. Commun. 1994, 2151.
91. Sufrin, J. R.; Lombardini, J. B.; Keith, D. D. Biochem. Biophys. Res. Commun. 1982, 706, 251.
92. Trost, B. M.; Bunt, R. C.Angew. Chem., Int. Ed. Engt. 1996, 35, 99.
93. Cameron, S.; Khambay, B. P. S. Tetrahedron Lett. 1998, 39, 1987.
94. N2′ reactions, see: Trost, B. M.; Klun, T. P. J. Org. Chem. 1980, 45, 4256-4257.
95. N2′ substitution is still a question, evidence shows the reversible formation of a cuprate-substrate (d-π*) complex in the initial step (Goering, H. L.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144.
96. Goering, H. L.; Seitz, E. P., Jr.; Tseng, C. C. J. Org. Chem. 1981, 46, 5304.
97. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984,25, 3063.).
98. To gain an understanding of the relative stabilities of two methylcopper-substrate (d-π*) complexes, we undertook ab initio calculations at the RHF/LANL1DZ level of theory. Effective core potential (ECP) for Cu and double-ξ were used for other elements. To reduce the size, two model systems A and B of methylcopper-substrate (d-π*) complexes were chosen. However, it was found that the energy difference between geometries A and B was predicted to be only 0.387 kcal/mol. Figure presented
99. (a) Lipshutz, B. H.; Sengupta, S. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1992; p 135.
100. (b) Lipshutz, B. H. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: London, 1995; Vol. 12, pp 59-130.
101. Ibuka, T.; Yamamoto, Y. In Organocopper Reagents; Taylor, R. J. K., Ed.; Oxford Unversity Press: Oxford, 1994; pp 154-157.
102. Ibuka, T.; Nakao, T.; Nishii, S.; Yamamoto, Y. J. Am. Chem. Soc. 1986,108, 7420.
103. (e) Ibuka, T.; Tanaka, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1989, 967.
104. (f) Ibuka, T.; Akimoto, N.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Org. Chem. 1989, 54, 4055.
105. (g) Ibuka, T.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Am. Chem. Soc. 1989, 111, 4864.
106. (h) Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1990, 29, 801.
107. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991,56, 4371.
108. Magid, R. M. Tetrahedron 1980, 36, 1901.
109. (a) Gallina, C.; Ciattini, P. G. J. Am. Chem. Soc. 1979, 101, 1035.
110. (b) Ganilla, C. Tetrahedron Lett. 1982,23, 3093.
111. Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715.
112. Fleming, I.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1986,1456.
113. (e) RajanBabu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, P. J. J. Am. Chem. Soc. 1988, 110, 7128.
114. (f) Greene, A. E.; Coelho, F.; Depres, J.P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661.
115. (g) Underiner, T. L.; Goering, H. L. J. Org. Chem. 1989, 54, 3239.
116. Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1985, 707, 6137.
117. Hutchinson, D. K.; Hardinger, S. A.; Fuchs, P. L. Tetrahedron Lett. 1986,27, 1425.
118. Hutchinson, D. K.; Fuchs, P. L. Tetrahedron Lett. 1986,27, 1429.
119. Pan, V.; Hutchinson, D. K.; Nantz, M. H.; Fuchs, P. L. Tetrahedron 1989,45,467.
120. Berglund, R. A.; Braish, T. F.; Jakubowski, J. A. Fuchs, P. L. Bioorg. Med. Chem. 1991, 7, 649.
121. Ziegler, F. E.; Cady, M. A. J. Org. Chem. 1981, 46, 122.
122. Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.; Gdmez, A. M. J. Org. Chem. 1990, 55, 2294.
123. Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207.
124. Roger, R.; Neilson, D. J. J. Chem. Soc. 1960, 627.
125. Johnson, R. A.; Hall, C. M.; Krueger, W. C.; Murray, H. C. Bioorg. Chem. 1973,2, 99.
126. Watson, M. B.; Youngson, G. W. J. Chem. Soc., Perkin Trans. 1 1972, 1597.