Asymmetric synthesis of primary amines by nucleophilic addition of alkyllithium compounds to aldehyde SAMP/RAMP hydrazones

Liebigs Annales

Volumn , Issue 6, 1997, Pages 1089-1100

  Enders, Dieter ^a   Nübling, Christoph ^a   Schubert, Heinrich ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric synthesis; Hydrazones; N N bond cleavage; Nucleophilic 1,2 addition; Primary amines

Indexed keywords

EID: 33748809991     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970608     Document Type: Article

References (87)

1. Preliminary communication: D. Enders, H. Schubert, C. Nübling, Angew. Chem. 1986, 98, 1118-1119;
2. Angew Chem., Int. Ed. Engl. 1986, 25, 1109-1110.
3. K. Harada in The Chemistry of the Carbon-Nitrogen Double Bond (Ed.: S. Patai), Interscience, London, 1969.
4. [3a] W. N. Speckamp, H. Hiemstra, Tetrahedron 1985, 41, 4367-4416.
5. [3b] P. S. Mariano, Acc. Chem. Res. 1983, 16, 130-137.
6. F. A. Davis, M. A. Giangiordano, W. E. Starner, Tetrahedron Lett. 1986, 27, 3957-3960.
7. C. Fuganti, P. Grasselli, G. Pedrocchi-Fantoni, J. Org. Chem. 1983, 48, 909-910.
8. [6a] R. Kober, K. Papadopoulos, W. Miltz, D. Enders, W. Steglich, H. Reuter, H. Puff, Tetrahedron 1985, 41, 1693-1701.
9. [6b] M. Hatanaka, H. Nitta, Tetrahedron Lett. 1987, 28, 69-72.
10. [7a] R. A. Volkmann, J. T. Davis, C. N. Meltz, J. Am. Chem. Soc. 1983, 105, 5946-5948.
11. [7b] D. A. Burnett, J. C. Galucci, D. J. Hart, J. Org. Chem. 1985, 50, 5120-5123.
12. [7c] L. S. Liebeskind, M. E. Welker, V. Goedken, J. Am. Chem. Soc. 1984, 106, 441-443.
13. M. Wada, Y. Sakurai, K. Akiba, Tetrahedron Lett. 1984, 25, 1079-1082.
14. [9a] G. E. Keck, E. J. Enholm, J. Org. Chem. 1985, 50, 146-147.
15. [9b] Y. Yamamoto, T. Komatsu, K. Maruyama, J. Org. Chem. 1985, 50, 3115-3121.
16. [9c] Y. Yamamoto, T. Komatsu, K. Maruyama, J. Am. Chem. Soc. 1984, 106, 5031-5033.
17. [9d] Y. Yamamoto, T. Komatsu, K. Maruyama, J. Chem. Soc. Chem. Commun. 1985, 814-816.
18. [9e] R. W. Hoffmann, G. Eichler, A. Endesfelder, Liebigs Ann. Chem. 1983, 2000-2007.
19. [9f] Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, W. Ito, J. Am. Chem. 1983, 2000-2007.
20. [9f] Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, W. Ito, J. Am. Chem. Soc. 1986, 108, 7778-7786.
21. D. Enders, H. Schubert, Angew. Chem. 1984, 96, 368-369;
22. Angew. Chem., Int. Ed. Engl. 1984, 23, 365-366.
23. [11a] H. Takahashi, Y. Suzuki, H. Inagaki, Chem. Pharm. Bull. 1982, 30, 3160-3166.
24. [11b] H. Takahashi, K. Tomita, H. Otomasu, J. Chem. Soc., Chem. Commun. 1979, 668-669.
25. [11c] H. Takahashi, K. Tomita, H. Naguchi, Chem. Pharm. Bull. 1981, 29, 3387-3391.
26. [11d] H. Takahashi, H. Inagaki, Chem. Pharm. Bull. 1982, 30, 922-926.
27. [11e] H. Takahashi, Y. Suzuki, Chem. Pharm. Bull. 1983, 31, 4295-4299.
28. [11f] Y. Suzuki, H. Takahashi, Chem. Pharm. Bull. 1983, 31, 31-40.
29. [11g] H. Takahashi, Y. Chida, T. Suzuki, S. Yanaura, Y. Suzuki, C. Masuda, Chem. Pharm. Bull. 1983, 31, 1659-1665.
30. [11h] H. Takahashi, Y. Suzuki, T. Hori, Chem. Pharm. Bull. 1983, 31, 2183-2191.
31. H. Schubert, Dissertation, University Bonn, 1985.
32. [13a] D. A. Claremon, P. K. Lumma, B. T. Phillips, J. Am. Chem. Soc. 1986, 108, 8265-8266.
33. [13b] R. K. Dieter, R. Datar, Can. J. Chem. 1993, 71, 814-823.
34. [13c] Y. H. Kim, J. Y. Choi, Tetrahedron Lett. 1996, 37, 5543-5546.
35. A. Alexakis, N. Lensen, J.-P. Tranchier, P. Mangeney, J. Org. Chem. 1992, 57, 4563-4565.
36. D. Enders, J. Tiebes, Liebigs Ann. Chem. 1993, 173-177.
37. C. Nübling, Dissertation, RWTH Aachen, 1987.
38. [17a] G. A. Molander, Chem. Rev. 1992, 29-68.
39. [17b] S. E. Denmark, T. Weber, D. W. Piotrowski, J. Am. Chem. Soc. 1987, 109, 2224-2225.
40. [17c] S. E. Denmark, O. Nicaise, Synlett 1993, 359-361.
41. [17d] S. E. Denmark, J. P. Edwards, O. Nicaise, J. Org. Chem. 1993, 58, 569-578.
42. A. Yanagisawa, K. Ogasawara, K. Yause, H. Yamamoto, J. Chem. Soc., Chem. Commun. 1996, 367-368.
43. [19a] D. Enders, J. Schankat, Helv. Chim. Acta 1995, 78, 970-992.
44. [19b] U. Veith, S. Leurs, V. Jäger, J. Chem. Soc., Chem. Commun. 1996, 329-330.
45. [19c] N. Meunier, U. Veith, V. Jäger, J. Chem. Soc., Chem. Commun. 1996, 331-332.
46. [19d] Y. Ukaji, J. Watai, T. Sumi, T. Fujisawa, Chem. Lett. 1991, 9, 1555-1558.
47. [19e] C. A. Willoughby, S. Buchwald, J. Am. Chem. Soc. 1992, 114, 7562-7564.
48. [20a] D. Enders, M. Meiers, Angew. Chem. 1996, 108, 2391-2393;
49. Angew. Chem., Int. Ed. Engl. 1996, 35, 2261-2263.
50. [20b] D. Enders, E. Chelain, Bull. Soc. Chim. Fr., in press.
51. [20c] D. Enders, U. Reinhold, Liebigs Ann. Chem. 1996, 11-26.
52. [20d] D. Enders, U. Reinhold, Angew. Chem. 1995, 107, 1332-1334;
53. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219-1222.
54. [20e] D. Enders, J. Schankat, M. Klatt, Synlett 1994, 795-797.
55. [20f] D. Enders, M. Klatt, R. Funk, Synlett ibid. 1993, 226-228.
56. [20g] D. Enders, R. Funk, M. Klatt, G. Raabe, E. R. Hovestreydt, Angew. Chem. 1993, 105, 418-420;
57. Angew. Chem., Int. Ed. Engl. 1993, 32, 418-421.
58. [20h] D. Enders, D. Bartzen, Liebigs Ann. 1991, 569-574.
59. D. Enders, H. Eichenauer, Chem. Ber. 1979, 112, 2933-2960.
60. H. G. O. Becker, G. Domschke, E. Fanghänel, M. Fischer, K. Gewald, R. Mayer, D. Pawel, H. Schmidt, K. Schwetlick, W. Berger, J. Faust, F. Gentz, R. Gluch, K. Müller, K. Schollberg, E. Seiler, G. Zeppenfeld, Organikum 15. ed., VEB Deutscher Verlag der Wissenschaften, Berlin 1977.
61. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
62. W. A. König, I. Benecke, S. Sievers, J. Chromatogr. 1982, 238, 427-432.
63. [25a] H. E. Smith, Chem. Rev. 1983, 83, 359-377.
64. [25b] H. E. Smith, E. P. Burrows, M. J. Marks, R. D. Lynch, F.-M. Chen, J. Am. Chem. Soc. 1977, 99, 707-713.
65. [25c] H. E. Smith, J. R. Neergaard, E. P. Burrows, F.-M. Chen, J. Am. Chem. Soc. 1974, 96, 2908-2916.
66. [25d] H. E. Smith, C. A. Taylor, A. F. McDonagh, F.-M. Chen, J. Org. Chem. 1982, 47, 2525-2531.
67. [25e] H. E. Smith, R. Records, Tetrahedron 1966, 22, 813-824.
68. [25f] H. E. Smith, F.-M. Chen, J. Org. Chem. 1979, 44, 2775-2779.
69. D. Enders, H. Eichenauer, R. Pieter, Chem. Ber. 1979, 112, 3703-3714.
70. S. E. Denmark, O. Nicaise, J. P. Edwards, J. Org. Chem. 1990, 55, 6219-6223.
71. W. A. König, Analysis of Volatiles, Walter de Gruyter, Berlin, 1984, p. 77.
72. Racemic amines rac-11 were prepared following standard literature procedures, based on reductive amination of carbonyl compounds.
73. Further details of the crystal structure investigation are available from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-59398.
74. [31a] D. Enders in Asymmetric Synthesis (Ed.: J. D. Morrison), Academic Press, New York, 1984, vol. 3, p. 275.
75. [31b] H. Eichenauer, Dissertation, University Gießen, 1980.
76. R. W. Kierstead, A. Faraone, F. Mennona, J. Mullin, R. W. Guthrie, H. Crowley, B. Simko, L. C. Blaber, J. Med. Chem. 1983, 26, 1561-1569.
77. [16].
78. P. Rademacher, H.-U. Pfeffer, D. Enders, H. Eichenauer, P. Weuster, J. Chem. Res. (S) 1979, 222-223;
79. J. Chem. Res. (M) 1979, 2501-2509.
80. L. Rüb, Dissertation, RWTH Aachen, 1987.
81. K. G. Davenport, H. Eichenauer, D. Enders, M. Newcomb, D. E. Bergbreiter, J. Am. Chem. Soc. 1979, 101, 5654-5659.
82. Sadtler-Katalog 1967, 8420 K; 3791 M.
83. W. H. Pirkle, T. G. Burlingame, S. D. Beare, Tetrahedron Lett. 1968, 5849-5852.
84. Sadtler-Katalog 1967, 2502 M;
85. Sadtler-Katalog 1974, 33213 K.
86. H. E. Smith, H. E. Ensley, Can. J. Chem. 1971, 49, 2902-2906.
87. P. A. Levine, A. Rothen, M. Kuna, J. Biol. Chem. 1937, 120, 759.