Practical and efficient synthesis of C2 symmetrical diamines with Zn / Me3SiCl

Synlett

Volumn , Issue 8, 1998, Pages 873-874

  Alexakis, Alexandre ^a   Aujard, Isabelle ^a   Mangeney, Pierre ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001629082     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1790     Document Type: Article

References (38)

1. Bennani Y.L., Hanessian S. Chem. Rev. 1997, 97, 3161-3195.
2. Alexakis A., Mangeney P. in Advanced Asymmetric Synthesis, Ed. G.R. Stephenson, Chapman & Hall, London, Chap. 5, 1996, 93-110.
3. Anselmino, O. Chem. Ber. 1908, 41, 621-623.
4. a) Neumann, W.P.; Werner, F. Chem. Ber. 1978, 111, 3904-3911.
5. b) Thies, H.; Schönenberger, H.; Bauer, K.H. Arch. Pharm. 1958, 291/63, 373-375.
6. Chem. Abstr. 1959, 53, 2127h.
7. c) Baruah, B.; Prajapati, D.; Sandhu, J.S. Tetrahedron Lett. 1995, 36, 6747-6750.
8. d) Nosek, J. Coll. Czech. Chem. Comm. 1967, 32, 2025-2028.
9. e) Betschart, C.; Seebach, D. Helv. Chim. Acta 1987, 70, 2215-2231.
10. f) Mangeney, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, J. Synthesis 1988, 255-257.
11. g) Stühmer, W.; Messwrb, G. Arch. Pharmaz. 1953, 286, 221-231.
12. Chem. Abstr. 1955, 49, 6192b.
13. h) Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811-3814.
14. i) Khan, N.H.; Zuberi, R.H.; Siddiqui, A.A. Synth. Comm. 1980, 10, 363-371.
15. j) Smith, J.G.; Boettger, T.J. Synth. Comm. 1981, 11, 61-64.
16. k) Shimizu, M.; Iida, T.; Fujisawa, T. Chem. Lett. 1995, 609-610.
17. l) Smith, J.G.; Veach, C.D. Can. J. Chem. 1966, 44, 2497-2502.
18. m) Smith, J.G.; Ho, I. J. Org. Chem. 1972, 37, 653-656.
19. n) Eisch, J.J.; Kaska, D.D.; Peterson, C.J. J. Org. Chem. 1966, 31, 453-456.
20. o) Schlenk, W.; Appenrodt, J.; Michael, A.; Thal, A.. Chem. Ber 1914, 47, 473-490.
21. p) Schlenk, W.; Bergmann, E. Liebigs Ann. Chem. 1928, 463, 281-322.
22. Chem. Abstr. 1928, 22, 4499.
23. q) Jaunin, R. Helv. Chim. Acta 1956, 39, 111-116.
24. r) Bachmann, E. J. Am. Chem. Soc. 1931, 53, 2672-2676.
25. s) Kalyanam, N.; Venkateswara Rao, G. Tetrahedron Lett. 1993, 34, 1647-1648.
26. t) Roskamp, E.J., Pedersen, S.F. J. Am. Chem. Soc. 1987, 109, 3152-3154.
27. u) Takaki, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203-204.
28. v) Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141-1142.
29. w) Enholm, E.J.; Forbes, D.C.; Holub, D.P. Synth. Comm. 1990, 20, 981-987.
30. x) Shono, T.; Kise, N.; Oike, H.; Yoshimoto, M.; Okazaki, E. Tetrahedron Lett. 1992, 33, 5559-5562.
31. y) Buchwald, S.L.; Watson, B.T.; Wannamaker, M.W.; Dewan, J.C. J. Am. Chem. Soc. 1989, 111, 4486-1494.
32. For a review see J. Boersma in Comprehensive Organometallic Chemistry, Ed. G. Wilkinson, 1982, Vol 2, p. 823-851.
33. Banerjee, A.K.; Sulbaran de Carrasco, M.C.; Frydrych-Houge, C., Motherwell, W.B., J. Chem. Soc., Chem. Comm. 1986, 1803-1805.
34. Grignon-Dubois, M., Fialeix, M., Can. J. Chem. 1993, 71, 754.
35. Zinc dust was purchased from Aldrich. Other sources of Zn work equally well.
36. The synthesis optically pure of N,N′-dimethyl-1,2-diphenyl-ethane-1,2-diamine 2a, by this coupling procedure, isomerization and resolution was submitted (and accepted) to Organic Syntheses (procedure no 2778).
37. 11 is obtained in 44% yield (16.5 g)
38. Cuvinot, D.; Mangeney, P.; Alexakis, A.; Normant, J.F. J. Org. Chem. 1989, 54, 2420-2425.