Asymmetric synthesis of 1,2-diamines by the addition of allylic zinc and magnesium reagents to N,N'-bis[(S)-1-phenylethyl)]ethanediimine

Synthesis

Volumn , Issue 4, 2000, Pages 581-587

  Alvaro, Giuseppe ^a   Grepioni, Fabrizia ^b   Grilli, Stefano ^c   Maini, Lucia ^c   Martelli, Gianluca ^c   Savoia, Diego ^c  

^a GSK   (Italy)

^b UNIVERSITY OF SASSARI   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Allylations; Amines; Asymmetric synthesis; Grignard reactions; Zinc

Indexed keywords

DIAMINE; IMINE; MAGNESIUM; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034128293     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6377     Document Type: Article

References (31)

1. The chemistry of vicinal 1,2-diamine has been recently reviewed: Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2580.
2. The chemistry of vicinal 1,2-diamine has been recently reviewed: Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161. Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2580.
3. Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
4. Roland, S.; Mangeney, P.; Alexakis, A. Synthesis 1999, 228.
5. Neumann, W.; Rogic, M. M.; Dunn, T. J. Tetrahedron Lett. 1991, 32, 5865.
6. Alvaro, G.; Grepioni, F.; Savoia, D. J. Org. Chem. 1997, 62, 4180.
7. Enders, D.; Meiers, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2261.
8. Alvaro, G.; Pacioni, P.; Savoia, D. Chem. Eur. J. 1997, 3, 726. Alvaro, G.; Martelli, G.; Savoia, D. J. Chem. Soc., Perkin Trans. 1 1998, 775.
9. Alvaro, G.; Pacioni, P.; Savoia, D. Chem. Eur. J. 1997, 3, 726. Alvaro, G.; Martelli, G.; Savoia, D. J. Chem. Soc., Perkin Trans. 1 1998, 775.
10. Alvaro, G.; Grilli, S.; Martelli, G.; Savoia, D. Eur. J. Org. Chem. 1999, 3, 1523.
11. Grepioni, F.; Grilli, S.; Martelli, G.; Savoia, D. J. Org. Chem. 1999, 64, 3679.
12. Basile, T.; Bocoum, A.; Savoia, D.; Umani-Ronchi, A. J. Org. Chem. 1994, 59, 7766.
13. Alvaro, G.; Savoia, D. Tetrahedron: Asymmetry 1996, 7, 2083.
14. Frangin, Y.; Gaudemar, M. Bull. Soc. Chim. Fr. 1975, 1173.
15. (a) Gerard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 1924.
16. (b) Gerard, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1974, 2527.
17. (c) The successful addition of pentadienylzinc bromide to an aldehyde by a Barbier procedure with ultrasonic activation of zinc has been described: Chen, L.-Y; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1181.
18. Miginiac, P.; Zamlouty, G. J. Organomet. Chem. 1975, 96, 163. Barbot, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1977, 113. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
19. Miginiac, P.; Zamlouty, G. J. Organomet. Chem. 1975, 96, 163. Barbot, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1977, 113. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
20. Miginiac, P.; Zamlouty, G. J. Organomet. Chem. 1975, 96, 163. Barbot, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1977, 113. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
21. Miginiac, P.; Zamlouty, G. J. Organomet. Chem. 1975, 96, 163. Barbot, F.; Miginiac, P. Bull. Soc. Chim. Fr. 1977, 113. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
22. Bates, R. B.; Gosselink, D. W.; Kaczynski, J. A. Tetrahedron Lett. 1967, 199. Bates, R. B.; Gosselink, D. W.; Kaczynski, J. A. Tetrahedron Lett. 1967, 205.
23. Bates, R. B.; Gosselink, D. W.; Kaczynski, J. A. Tetrahedron Lett. 1967, 199. Bates, R. B.; Gosselink, D. W.; Kaczynski, J. A. Tetrahedron Lett. 1967, 205.
24. The preparation of 2,4-pentadienylzinc bromide from pentadienyl potassium was previously described: Yasuda, H.; Ohnuma, Y.; Nakamura, A.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1980, 53, 1101.
25. The addition of 3-butenylzinc bromide to aldehyde and imines gave mixtures of syn-and anti-diastereomers: Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Organomet. Chem. 1985, 285, 31. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
26. The addition of 3-butenylzinc bromide to aldehyde and imines gave mixtures of syn-and anti-diastereomers: Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Organomet. Chem. 1985, 285, 31. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
27. The addition of 3-butenylzinc bromide to aldehyde and imines gave mixtures of syn-and anti-diastereomers: Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Organomet. Chem. 1985, 285, 31. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
28. The addition of 3-butenylzinc bromide to aldehyde and imines gave mixtures of syn-and anti-diastereomers: Courtois, G.; Miginiac, L. J. Organomet. Chem. 1974, 69, 1. Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Organomet. Chem. 1985, 285, 31. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. J. Am. Chem. Soc. 1986, 108, 7778. Taniguchi, M.; Oshima, K.; Utimoto, K. Chem. Lett. 1992, 2135.
29. (a) Sheldrick, G. M. SHELXL97, Program for Crystal Structure Determination; University of Göttingen; Göttingen, Germany, 1997.
30. (b) Keller, E. SCHAKAL97, Graphical Representation of Molecular Models; University of Freiburg, Germany, 1997.
31. The author has deposited atomic coordinates for these structures at the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.