Diastereo- and enantioselective synthesis of C2-symmetric, protected 1,n-diamines from dialdehydes

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 19, 1996, Pages 2261-2263

  Enders, Dieter ^a   Meiers, Michaela ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric syntheses; Diamines; Hydrazones; Nucleophilic additions; Synthetic methods

Indexed keywords

EID: 0030459043     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199622611     Document Type: Article

References (25)

1. a) S. Hanessian, D. Delorme, S. Beaudoin, Y. Leblanc, J. Am. Chem. Soc. 1984, 106, 5754;
2. b) E. J. Corey, Pure Appl. Chem. 1990, 62, 1209, and references therein;
3. c) E. J. Corey, S. S. Kim, J. Am. Chem. Soc. 1990, 112, 4976;
4. d) V. J. Blazis, K. J. Koeller, C. D. Spilling, Tetrahedron: Asymmetry 1994, 5, 499.
5. a) S. G. Davies, A. A. Mortlock, Tetrahedron 1993, 49, 4419;
6. b) S. G. Davies, G. B. Evans, A. A. Mortlock, Tetrahedron; Asymmetry 1994, 5, 585;
7. c) A. Alexakis, R. Sedrani, N. Lensen, P. Mageney in Organic Synthesis via Organometallics (Eds.: D. Enders, H.-J. Gais, W. Keim), Vieweg, Braunschweig, 1993, p. 1;
8. d) A. Alexakis, N. Lensen, J.-P. Tranchier, P. Mangeney, J. Feneau-Dupont, J. P. Declercq, Synthesis 1995, 1038;
9. e) A. Alexakis, T. Ranger, P. Mangeney, F. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 47;
10. f) A. Alexakis, J.-P. Tranchier, N. Lensen, P. Mangeney, J. Am. Chem. Soc. 1995, 117, 10767;
11. g) A. Alexakis, P. Mangeney, N. Lensen, J.-P. Tranchier, R. Gosmini, S. Raussou, Pure Appl. Chem. 1996, 68, 531.
12. Latest examples: a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521; b) Y. Nishibayashi, Y. Arikawa, K. Ohe, S. Uemura, J. Org. Chem. 1996, 61, 1172; c) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675; d) A. Alexakis, T. Kanger, P. Mangeney, R. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 2135; e) P. Gamez, F. Fache, M. Lemaire, ibid. 1995, 6, 705; f) M. Nakajima, K. Tomioka, K. Koga, Tetrahedron 1993, 49, 9735.
13. Latest examples: a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521; b) Y. Nishibayashi, Y. Arikawa, K. Ohe, S. Uemura, J. Org. Chem. 1996, 61, 1172; c) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675; d) A. Alexakis, T. Kanger, P. Mangeney, R. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 2135; e) P. Gamez, F. Fache, M. Lemaire, ibid. 1995, 6, 705; f) M. Nakajima, K. Tomioka, K. Koga, Tetrahedron 1993, 49, 9735.
14. Latest examples: a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521; b) Y. Nishibayashi, Y. Arikawa, K. Ohe, S. Uemura, J. Org. Chem. 1996, 61, 1172; c) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675; d) A. Alexakis, T. Kanger, P. Mangeney, R. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 2135; e) P. Gamez, F. Fache, M. Lemaire, ibid. 1995, 6, 705; f) M. Nakajima, K. Tomioka, K. Koga, Tetrahedron 1993, 49, 9735.
15. Latest examples: a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521; b) Y. Nishibayashi, Y. Arikawa, K. Ohe, S. Uemura, J. Org. Chem. 1996, 61, 1172; c) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675; d) A. Alexakis, T. Kanger, P. Mangeney, R. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 2135; e) P. Gamez, F. Fache, M. Lemaire, ibid. 1995, 6, 705; f) M. Nakajima, K. Tomioka, K. Koga, Tetrahedron 1993, 49, 9735.
16. Latest examples: a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521; b) Y. Nishibayashi, Y. Arikawa, K. Ohe, S. Uemura, J. Org. Chem. 1996, 61, 1172; c) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675; d) A. Alexakis, T. Kanger, P. Mangeney, R. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 2135; e) P. Gamez, F. Fache, M. Lemaire, ibid. 1995, 6, 705; f) M. Nakajima, K. Tomioka, K. Koga, Tetrahedron 1993, 49, 9735.
17. Latest examples: a) A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521; b) Y. Nishibayashi, Y. Arikawa, K. Ohe, S. Uemura, J. Org. Chem. 1996, 61, 1172; c) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675; d) A. Alexakis, T. Kanger, P. Mangeney, R. Rose-Munch, A. Perrotey, E. Rose, Tetrahedron: Asymmetry 1995, 6, 2135; e) P. Gamez, F. Fache, M. Lemaire, ibid. 1995, 6, 705; f) M. Nakajima, K. Tomioka, K. Koga, Tetrahedron 1993, 49, 9735.
18. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
19. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
20. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
21. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
22. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
23. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
24. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.
25. Latest examples: a) J.-X. Gao, T. Ikariya, R. Noyori, Organometallics 1996, 15, 1087; b) B. M. Trost, Z. Shi. J. Am. Chem. Soc. 1996, 118, 3037; c) B. M. Trost, R. C. Bunt, Angew. Chem. 1996, 108, 70; Angew. Chem. Int. Ed. Engl. 1996, 35, 70; d) X. Zhang, C. Guo, Tetrahedron Lett. 1995, 36, 4947; e) S. E. Denmark, B. L. Christenson, S. P. O'Connor, ibid. 1995, 36, 2219; f) A. Vaupel, P. Knochel, ibid. 1995, 36, 231; g) H. Takahashi, M. Yoshioka, M. Shibasaki, M. Ohno, N. Imai, S. Kobayashi, Tetrahedron 1995, 51, 12013.