Recent advancements in the homoallylamine chemistry

Journal of Heterocyclic Chemistry

Volumn 39, Issue 4, 2002, Pages 595-614

  Ochoa Puentes, Cristian ^a   Kouznetsov, Vladimir ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

Author keywords

Allylation; Homoallylic amines; Intramolecular cyclizations; Saturated nitrogen heterocycles; Sigmatropic rearrangements

Indexed keywords

ALLYLAMINE DERIVATIVE; AMMONIUM DERIVATIVE; AZETIDINE DERIVATIVE; BENZAZEPINE DERIVATIVE; HETEROCYCLIC COMPOUND; HOMOALLYLAMINE DERIVATIVE; IMINE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036666324     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570390401     Document Type: Review

References (147)

1. M. Johannsen and K. A. Jørgensen, Chem. Rev., 98, 1689 (1998).
2. R. B. Cheikh, R. Caabouni, A. Laurent, P. Mison and A. Nafti, Synthesis, 685 (1983).
3. W. R. Rouch, In Comprehensive Organic Synthesis, Vol. 2, B. M. Trost and I. Fleming, eds., Pergamon Press, Oxford, 1994, pp.1-53.
4. R. Bloch, Chem. Rev., 98, 1407 (1998).
5. Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993).
6. R. A. Volkmann, Additions to C-X π-Bonds, Part 1, in Comprehensive Organic Synthesis, Vol. 1, B. M. Trost and I. Fleming, eds., Pergamon Press, Oxford, 1991, pp. 355-396.
7. E. F. Kleinman and R. A. Volkmann, Additions to C-X πBonds, Part 2, in Comprehensive Organic Synthesis, Vol. 2, B. M. Trost and I. Fleming, eds., Pergamon Press, Oxford, 1991, pp. 975-1006.
8. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999).
9. D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 8, 1895 (1997).
10. S. E. Denmark and O. J. C. Nicaise, J. Chem. Soc., Chem. Commun., 999 (1996).
11. C. Blomberg, The Barbier reaction and Related One-Step Processes, Springer-Verlag, Berlin, Heidelberg, 1993.
12. B. J. Wakefield, Organomagnesium Methods in Organic Synthesis, Best Synthetic Methods series, A. R. Katrizky, O. Meth-Cohn and C. W. Rees, eds., Academic Press, San Diego, 1995.
13. A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Chem., Perkin Trans. 1, 1542 (1993).
14. G. Alvaro, G. Martelli and D. Savoia, J. Chem., Perkin Trans. 1, 775 (1998).
15. G. Alvaro, C. Boga, D. Savoia and A Umani-Ronchi, J. Chem., Perkin Trans. 1, 875 (1996).
16. M. van der Sluis, J. Dalmolen, B. de Lange, B. Kaptein, R. M. Kellogg and Q. B. Broxterman, Org. Lett., 3, 3943 (2001).
17. A. Zwierzak and A. Napieraj, Synthesis, 930 (1999).
18. A. Yanagisawa, K. Ogasawara, K. Yasue and H. Yamamoto, Chem. Commun., 367 (1996).
19. W. Su, J. Li and Y. Zhag, Synth. Commun., 31, 273 (2001).
20. H. Tanaka, K. Inoue, U. Pokorski, M. Taniguchi and S. Torii, Tetrahedron Lett., 31, 3023 (1990).
21. T. Basile, A. Bocoum, D. Savoia and A. Umani-Ronchi, J. Org. Chem., 59, 7766 (1994).
22. R. Yanada, M. Okaniwa, A. Kaieda, T. Ibuka and Y. Takemoto, J. Org. Chem., 66, 1283 (2001).
23. R. Yanada, A. Kaieda and Y. Takemoto, J. Org. Chem., 66, 7516 (2001).
24. A. A. El-Shehawy, M. A. Omara, K. Ito and S. Itsuno, Synlett, 367 (1998).
25. C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 93, 1371 (1993).
26. D.-K. Wang, Y.-G. Zhou, Y. Tang, X.-L. Hou and L.-X. Dai, J. Org. Chem., 64, 4233 (1999).
27. A. S. Pilcher and P. DeShong, J. Org. Chem. 61, 6901 (1996).
28. K. Nakamura, H. Nakamura and Y. Yamamoto, J. Org. Chem., 64, 2614 (1999).
29. P. Del Buttero, E. Licandro, A. Papagni, M. Lanfranchi and A. Tiripicchio, J. Organometallic Chem., 593/594, 380 (2000).
30. W. Lu and T. H. Chan, J. Org. Chem., 66, 3467 (2001).
31. J. V. Schaus, N. Jain and J. S. Panek, Tetrahedron, 56, 10263 (2000).
32. D. M. Spero and S. R. Kapadia, J. Org. Chem., 62, 5537 (1997).
33. S. Itsuno, K. Watanabe, K. Ito, A. A. El-Shehawy and A. A. Sarhan, Angew. Chem. Int. Ed. Engl., 36, 109 (1997).
34. S. Itsuno, K. Watanabe, T. Matsumoto, S. Kuroda, A. Yokoi and A. A. El-Shehawy, J. Chem. Soc., Perkin Trans. 1, 2011 (1999).
35. G.-M. Chen, P. V. Ramachandran and H. C. Brown, Angew. Chem. Int. Ed. Engl., 38, 825 (1999).
36. K. Watanabe, S. Kuroda., A. Yokoi, K. Ito and S. Itsuno, J. Organometallic Chem., 581, 103 (1999).
37. X. Fang, M. Johannsen, S. Yao, N. Cathergood, R. G. Hazell and K. A. Jørgensen, J. Org. Chem., 64, 4844 (1999).
38. J. C. A. Hunt, C. Lloyd, C. J. Moody, A. M. Z. Slawin and A. K. Takle, J. Chem. Soc., Perkin Trans. 1, 3443 (1999).
39. H. M. S. Kumar, S. Anjaneyulu, E. J. Reddy and J. S. Yadav, Tetrahedron Lett., 41, 9311 (2000).
40. S. Kobayashi and R. Hirabayashi, J. Am. Chem. Soc., 121, 6942 (1999).
41. M. Bao, H. Nakamura and Y. Yamamoto, Tetrahedron Lett., 41, 131 (2000).
42. S. Itsuno, K. Watanabe and A. A. El-Shehawy, Adv. Synth. Catal., 343, 89 (2001).
43. S. D. Larsen, P. A. Grieco and W. F. Fobare, J. Am. Chem. Soc., 108, 3512 (1986).
44. R. A. Grieco and A. Bahsas, J. Org. Chem., 52, 1378 (1987).
45. S. Kobayashi, T. Busujima and S. Nagayama, Chem. Commun., 19 (1998).
46. S. Kobayashi, S. Kasumi and H. Oyamada, Synlett, 138 (1999).
47. S. Kobayashi, T. Hamada and K. Marabe, Synthesis, 1140 (2001).
48. S. J. Venstra and P. Schimd, Tetrahedron Lett., 38, 997 (1997).
49. M. Billet, P. Klotz and A. Mann, Tetrahedron Lett., 42, 631 (2001).
50. Y. Masuyama, J. Tosa and Y. Kurusu, Chem. Commun., 1075 (1999).
51. M. Roux, M. Santelli and J. L. Parain, Org. Lett., 2, 1701 (2000).
52. H. C. Aspinall, J. S. Bissett, N. Greeves and D. Levin, Tetrahedron Lett., 42, 323 (2001).
53. W. J. N. Meester, F. P. T. T. Rutjes, P. H. H. Hermkens and H. Hiemstra, Tetrahedron Lett., 40, 1601 (1999).
54. R. E. Ireland and R. H. Mueller, J. Am. Chem. Soc., 94, 5897 (1972).
55. R. E. Ireland, R. H. Mueller and A. K. Willard, J. Am. Chem. Soc., 98, 2868 (1976).
56. P. A. Bartlett and J. F. Barstow, J. Org. Chem., 47, 3933 (1982).
57. U. Kazmaier, Angew. Chem., Int. Ed. Engl., 33, 998 (1994).
58. U. Kazmaier, Synlett, 1138 (1995).
59. U. Kazmaier, J. Org. Chem., 61, 3694 (1999).
60. M. Mohamed and M. A. Brook, Tetrahedron Lett., 42, 191 (2001).
61. U. Kazmaier, Tetrahedron, 50, 12895 (1994).
62. T. Hudlicky, K. Oppong, C. Duan, C. Stanton, M. J. Laufersweiler and M. G. Natchus, Bioorg. Med. Chem. Lett., 11, 627 (2001).
63. U. Kazmaier, J. Org. Chem., 59, 6667 (1994).
64. I. Coldham, M. L. Middleton and P. L. Taylor, J. Chem. Soc., Perkin Trans. 1, 2951 (1997).
65. J. C. Anderson, D. C. Siddons, S. C. Smith and M. E. Swarbrick, J. Chem. Soc., Chem. Commun., 1835 (1995).
66. J. C. Anderson, D. C. Siddons, S. C. Smith and M. E. Swarbrick, J. Org. Chem., 61, 4820 (1996).
67. J. C. Anderson, S. C. Smith and M. E. Swarbrick, J. Chem. Soc., Perkin Trans. 1, 1517 (1997).
68. J. C. Anderson, P. Dupau, D. C. Siddons, S. C. Smith and M. E. Swarbrick, Tetrahedron Lett., 39, 2649 (1998).
69. S. Manabe, Tetrahedron Lett., 38, 2491 (1997).
70. Y. Murata and T. Nakai, Chem. Lett., 2069 (1990).
71. S. V. Kessar, P. Singh, K. N. Singh, V. K. Kaul and G. Kumar, Tetrahedron Lett., 36, 8481 (1995).
72. I. Coldham, M. L. Middleton and P. L. Taylor, J. Chem. Soc., Perkin Trans. 1, 2817 (1998).
73. T. Shimada, A. Fujimoto, T. Takagi, A. Koyama, A. Ando and I. Kumadaki, Heterocycles, 40, 753 (1995).
74. F. Henin, E. Mahuet, C. Muller and J. Muzart, Synth. Commun., 25, 1331 (1995).
75. K. W. Laue and G. Haufe, Synthesis, 1453 (1998).
76. T. Okino and Y. Takemoto, Org. Lett., 3, 1515 (2001).
77. L. Shikui, M. Aiqiao, W. Lanjun and J. Yaozhong, Synth. Commun., 23, 2485 (1993).
78. H.-J. Breternitz and E. Schaumann, J. Chem. Soc., Perkin Trans. 1, 1927 (1999).
79. R. P. Bonar-Law, A. P. Davis and B. J. Dorgan, Tetrahedron Lett., 31, 6725 (1990).
80. T. Ibuka, H. Habashita, A. Otaka, N. Fujii, Y. Oguchi, T. Uyehara and Y. Yamamoto, J. Org. Chem., 56, 4370 (1991).
81. R. Polt, M. A. Peterson and L. DeYuong, J. Org. Chem., 57, 5469 (1992).
82. S. R. Angle and R. M. Henry, J. Org. Chem., 62, 8549 (1997).
83. K.-Y. Lee, Y.-H. Kim, M.-S. Park, C.-Y. Oh and W.-H. Ham, J. Org. Chem., 64, 9450 (1999).
84. C. Douat, A. Heitz, J. Martinez and J.-A. Fehrentz, Tetrahedron Lett., 42, 3319 (2001).
85. B. Choucair, H. Léon, M.-A. Miré, C. Lebreton and P. Mosset, Org. Lett., 2, 1851 (2000).
86. J. P. Morken, M. T. Didiuk and A. H. Hoveyda, J. Am. Chem. Soc., 115, 6997 (1993).
87. M. S. Visser, N. M. Heron, M. T. Didiuk; J. F. Sagal and A. H. Hoveyda, J. Am. Chem. Soc., 118, 4291 (1996).
88. J. E. Balwin, J. Chem. Soc., Chem. Commun., 734 (1976).
89. J. E. Balwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman and R. C. Thomas, J. Chem. Soc., Chem. Commun., 734 (1976).
90. M. B. Smith, "Organic Synthesis: Theory, Reactions, and Methods" McGram-Hill, Inc., N.-Y., 1994, pp. 602-611.
91. N. S. Prostakov, V. V. Kuznetsov and E. E. Stashenko, Khim. Geterotsikl. Soedin., 1514 (1989); Chem. Abst., 113, 40.424z (1990).
92. N. S. Prostakov, V. V. Kuznetsov and E. E. Stashenko, Khim. Geterotsikl. Soedin., 1514 (1989); Chem. Abst., 113, 40.424z (1990).
93. L. Y. Vargas, W. Rozo and V. Kouznetsov, Heterocycles, 53, 785 (2000).
94. S. Robin and G. Rousseau, Eur. J. Org. Chem., 3007 (2000).
95. C. Vanucci, X. Brusson, V. Verdel, F. Zana, H. Dhiumane and G. Lhommet, Tetrahedron Lett., 36, 2971 (1995).
96. B. Giese, "Radical in Organic Synthesis: Formation of Carbon-Carbon Bonds", Pergamon Press, Oxford, 1986.
97. D. P. Curran, Synthesis, 417 (1988).
98. C. P. Jasperse, D. P. Curran and T. L. Fevig, Chem. Rev., 91, 1237 (1991).
99. P. Arya and D. D. M. Wayner, Tetrahedron Lett., 32, 6265 (1991).
100. D. Kuznich, S. C. Wu, D.-C. Ha, C.-S. Lee, S. Ramesh, S. Armes, S. Atarashi, J.-K. Choi and D. J. Hart, J. Am. Chem. Soc., 116, 6943 (1994).
101. G. Pandey, G. Kumaraswamy and U. T. Bhalerao, Tetrahedron Lett., 30, 6059 (1989).
102. A. Pawda, H. Nimmesgern and G. K. S. Wong, J. Org. Chem., 50, 5620 (1985).
103. M. Jonas, S. Blechert and E. Steckhan, J. Org. Chem., 66, 6896 (2001).
104. A. R. Katritzky, D. Feng, M. Qi, J. M. Aurrecoechea, R. Suero and N. Aurrekoetxea, J. Org. Chem., 64, 3335 (1999).
105. E. W. Della and P. A. Smith, J. Org. Chem., 64, 1798 (1999).
106. A. Barco, S. Benetti, A. Casolari, G. P. Pollini and G. Spalluto, Tetrahedron Lett., 31, 3039 (1990).
107. I. Coldham and R. Hufton, Tetrahedron Lett., 36, 2157 (1995).
108. I. Coldham, R. Hufton and R. E. Rathmell, Tetrahedron Lett., 38, 7617 (1997).
109. E. Lorthiois, I. Marek and J. F. Normant, Tetrahedron Lett., 38, 89 (1997).
110. P. Karoyan and G. Chassaing, Tetrahedron Lett., 38, 85 (1997).
111. E. Lorthiois, I. Marek and J. F. Normant, J. Org. Chem., 63, 2442 (1998).
112. K. M. Brummond and J. Lu, Org. Lett., 3, 1347 (2001).
113. S. Tanako, Y. Iwabuchi and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1527 (1988).
114. A. D. Jones and D. W. Knight, Chem. Commun., 915 (1996).
115. D. W. Knight, A. L. Redfern and J. Gilmore, Tetrahedron Lett., 39, 8909 (1998).
116. D. W. Knight, A. L. Redfern and J. Gilmore, Synlett, 731 (1998).
117. S. Deloisy, H. Tietgen and H. Kunz, Collect. Czech. Chem. Commun., 65, 816 (2000).
118. A. R. Katritzky, L. Zhang, J. Yao, O. V. Denisko, J. Org. Chem., 65, 8074 (2000).
119. M. Eguchi, Q. Zeng, A. Korda and I. Ojima, Tetrahedron Lett., 34, 915 (1993).
120. I. Ojima, M. Tzamarioudaki and M. Eguchi, J. Org. Chem., 60, 7078 (1995).
121. P. Schwab, M. B. France, J. W. Seller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 34, 2039 (1995).
122. A. J. Phillips and A. D. Abell, Aldrichimica Acta, 32, 75 (1999).
123. T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 34, 18 (2001).
124. J. Pernerstorfer, M. Schuster and S. Blechert, Synthesis, 138 (1999).
125. F. L. Zumpe and U. Kazmaier, Synthesis, 1785 (1999).
126. W. H. Pearson and A. Aponick, Org. Lett., 3, 1327 (2001).
127. S. S. Kinderman, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra and F. P. J. T. Rutjes, Org. Lett., 3, 2045 (2001).
128. C. J. Creighton and A. B. Reitz, Org. Lett., 3, 893 (2001).
129. G. Alvaro, G. Martelli, D. Savoia and A. Zoffoli, Synthesis, 1773 (1998).
130. Y. M. Xu and W.-S. Zhou, Tetrahedron Lett., 37, 1461 (1996).
131. L.-X. Liao and W.-S. Zhou, Tetrahedron, 54, 12571 (1998).
132. A. J. Clark, K. Jones, C. McCArthy and J. M. D. Storey, Tetrahedron Lett., 32, 2829 (1991).
133. V. V. Kuznetsov, E. I. Andreeva and N. S. Prostakov, Khim.Farm. Zh., 29, 61 (1995); Chem. Abstr., 124, 48,290 (1996).
134. V. V. Kuznetsov, E. I. Andreeva and N. S. Prostakov, Khim.Farm. Zh., 29, 61 (1995); Chem. Abstr., 124, 48,290 (1996).
135. V. Kouznetsov, J. Urbina, A. Palma, S. López, C. Devia, D. Enriz and S. Zacchino, Molecules, 5, 428 (2000).
136. J. M. Urbina, J. C. Cortés, A. Palma, S. N. López, S. A. Zacchino, D. R. Enriz, J. C. Ribas and V. Kouznetsov, Bioorg. Med. Chem., 8, 691 (2000).
137. V. V. Kuznetsov, A. E. Aliev and N. S. Prostakov, URSS Patent, 1,696,429 (1991); Chem. Abstr., 117, 48,356g (1992).
138. V. V. Kuznetsov, A. E. Aliev and N. S. Prostakov, Khim. Geterotsikl. Soedin., 73 (1994); Chem. Abst., 121, 300.783 (1994).
139. V. V. Kuznetsov, A. E. Aliev and N. S. Prostakov, Khim. Geterotsikl. Soedin., 73 (1994); Chem. Abst., 121, 300.783 (1994).
140. L. Y. Vargas Méndez, V. Kouznetsov, E. Slashenko, A. Bahsas and J. Amaro-Luis, Heterocyclic Commun., 7, 323 (2001).
141. V. V. Kouznetsov, A. R. Palma and A. E. Aliev, Anales de Química. Int. Ed., 94, 132 (1998).
142. N. Öcal, Ç. Yolaçan, Ş. Kahan, M. L. Y. Vargas and V. Kouznetsov, J. Heterocyclic Chem., 38, 233 (2001).
143. L. Y. Vargas Méndez, V. Kouznetsov, J. C. Poveda, C. Yolaçan, N. Öcal and F. Aydoǧan, Heterocyclic Commun., 7, 129 (2001).
144. V. Kouznetsov, Rev. Soc. Quire. Méx., 43, 30 (1999).
145. V. V. Kuznetsov and N. S. Prostakov, Khim. Geterotsikl. Soedin., 3 (1994); Chem. Abstr., 121, 255,518 (1994).
146. V. V. Kuznetsov and N. S. Prostakov, Khim. Geterotsikl. Soedin., 3 (1994); Chem. Abstr., 121, 255,518 (1994).
147. V. Kouznetsov, A. Palma and C. Ewert, Curr. Org. Chem., 5, 519 (2001).