A simple and efficient method for the preparation of homochiral amines: Application to the synthesis of a new C2 symmetric triamine

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5619-5622

  O'Brien, Peter ^a   Poumellec, Pierre ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; PIPERIDINE DERIVATIVE; POLYAMINE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01140-9     Document Type: Article

References (18)

1. 1. Bhuniya, D.; Gupta, A. D.; Singh, V. K. Tetrahedron Lett., 1995, 36, 2847-2850.
2. 2. Bhuniya, D.; Singh, V. K. Synth. Commun., 1994, 24, 1475-1481.
3. 3. Kim, H.; Shirai, R.; Kawasaki, H.; Nakajima, M.; Koga, K. Heterocycles, 1990, 30, 307-310; Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc., 1986, 108, 543-545.
4. 3. Kim, H.; Shirai, R.; Kawasaki, H.; Nakajima, M.; Koga, K. Heterocycles, 1990, 30, 307-310; Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc., 1986, 108, 543-545.
5. 4. Rossiter, B. E.; Eguchi, M.; Miao, G.; Swingle, N. M.; Hernández, A. E.; Vickers, D.; Fluckiger, E.; Patterson, R. G.; Reddy, K. V. Tetrahedron, 1993, 49, 965-986.
6. 5. Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem., 1991, 34, 181-189. See also: Chang, A-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. J. Med. Chem., 1994, 37, 4490-4498; Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864.
7. 5. Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem., 1991, 34, 181-189. See also: Chang, A-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. J. Med. Chem., 1994, 37, 4490-4498; Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864.
8. 5. Costello, G. F.; James, R.; Shaw, J. S.; Slater, A. M.; Stutchbury, N. C. J. J. Med. Chem., 1991, 34, 181-189. See also: Chang, A-C.; Takemori, A. E.; Ojala, W. H.; Gleason, W. B.; Portoghese, P. S. J. Med. Chem., 1994, 37, 4490-4498; Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864. Weerawarna, S. A.; Davis, R. D.; Nelson, W. L. J. Med. Chem., 1994, 37, 2856-2864.
9. 6. For example, footnote 8 in: Denis, J-N.; Correa, A.; Greene, A. E. J. Org. Chem., 1991, 56, 6939-6942.
10. 7. The details of the modified synthetic route are described in footnote 15 (see reference 1).
11. 8. Shirai, R.; Aoki, K.; Sato, D.; Kim, H-D.; Murakata, M.; Yasukata, T.; Koga, K. Chem. Pharm. Bull., 1994, 42, 690-693.
12. 9. Dieter, R. K.; Lagu, B.; Dieter, J. W.; Deo, N.; Pennington, W. T. Synlett, 1990, 109-110.
13. 10. Miao, G.; Rossiter, B. E. J. Org. Chem., 1995, 60, 8424-8427.
14. 11. (R)-and (S)-Styrene oxide are available from Aldrich Chemical Company Ltd.
15. BOH) and 3.54 (1 H, t, J 5.8, PhCHN).
16. 13. This is a vigorously stirred two phase reaction which requires 16 hours to reach completion.
17. 14. For leading references on the use of other aziridinium ions in synthesis, see: Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett., 1995, 36, 9241-9244; Liu, Q.; Simms, M. J.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1, 1994, 1363-1365.
18. 14. For leading references on the use of other aziridinium ions in synthesis, see: Richardson, P. F.; Nelson, L. T. J.; Sharpless, K. B. Tetrahedron Lett., 1995, 36, 9241-9244; Liu, Q.; Simms, M. J.; Boden, N.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1, 1994, 1363-1365.