Rapid access to enantiopure bicyclic diamines via aza-Diels-Alder reaction of iminoamides

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6736-6738

  Modin, Stefan A ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; EPOXIDATION; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034613219     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo005508z     Document Type: Article

References (18)

1. For a review of the chemistry of vicinal diamines see: Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580.
2. (a) O'Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439.
3. (b) de Sousa, S. E.; O'Brien, P.; Steffens, H. C. Tetrahedron Lett. 1999, 40, 8423.
4. Clayden, J.; Lai, L. W. Angew. Chem. Int. Ed. 1999, 38, 2556.
5. (a) Pénicaud, V.; Maillet, C.; Janvier, P.; Pipelier, M.; Bujoli, B. Eur. J. Org. Chem. 1999, 1745, 5.
6. (b) Tommasino, M. L.; Thomazeau, C.; Touchard, F.; Lemaire, M. Tetrahedron: Asymmetry 1999, 10, 1813.
7. (c) Murata, K.; Ikariya, T.; Noyori, R. J. Org. Chem. 1999, 64, 2186.
8. (a) Södergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760.
9. (b) Södergren, M. J.; Bertilsson, S. K.; Andersson, P. G. J. Am. Chem. Soc. 2000, 122, 6610.
10. (a) Stella, L.; Abraham, H.; Feneau-Dupont, J.; Tinant, B.; Declercq, J. P. Tetrahedron Lett. 1990, 31, 2603.
11. (b) Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707.
12. Brandt, P.; Andersson, P. G. Synlett 2000, 1092.
13. (a) von Seebach, D.; Dörr, H.; Bastani, B.; Ehrig, V. Angew. Chem. 1969, 81, 1002.
14. (b) Marx, M. A.; Grillot, A.-L.; Louer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153.
15. (c) Raczko, J.; Achmatowicz, M.; Jezewski, A.; Chapuis, C.; Urbanczyk-Lipkowska, Z.; Jurczak, J. Helv. Chim. Acta 1998, 81, 1264.
16. (d) Frankland, P. F.; Ormerod, E. J. Chem. Soc. 1903, 83, 1343.
17. (e) Frankland, P. F.; Twiss, D. F. J. Chem. Soc. 1910, 97, 154.
18. Suzuki, M.; Kimura, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1986, 59, 3559.