Diastereoselective one-step synthesis of functionalized cis-aziridinyl alcohols from oxiranyl carbaldimines

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3267-3270

  Bilke, Julia Luzia ^a   Dzuganova, Monika ^a   Fröhlich, Roland ^a   Würthwein, Ernst Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23044508036     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051090l     Document Type: Article

References (21)

1. McCoull, W.; Davis, F. A. Synthesis 2000, 1347-1365.
2. Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258.
3. Tanner, D. Angew. Chem. 1994, 106, 625-646;
4. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-616.
5. Coutrot, P.; El Gadi, A. J. Organomet. Chem. 1985, 280, C-11.
6. Alickmann, D.; Fröhlich, R.; Würthwein, E.-U. Org. Lett. 2001, 10, 1527-1530.
7. Compare: Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065-5068.
8. Kim, S.-W.; Noh, H.-Y.; Paek, S. I.; Ha, H.-J.; Lee, W. K. Bull. Korean Chem. Soc. 2004, 25, 1617-1618.
9. 25NO (247.38): C, 77.68; H, 10.19; N, 5.66. Found: C, 77.70; H, 10.15; N, 5.49.
10. Ceroni, M.; Séquin, U. Helv. Chim. Acta 1982, 65, 302-316.
11. Taguchi, K.; Westheimer, F. H. J. Org. Chem. 1971, 36, 1579-1572.
12. Schaer, C. Helv. Chim. Acta 1958, 41, 619-623.
13. Tishenko, I. G.; Revinskii, I. F.; Grinkevich, V. G.; Suboch, V. P. USSR Vestn. Beloruss. Un-ta, Ser. 2 1978, 1, 28-32; CAN 90:71968 (1979).
14. For a review, see: Ibuka, T. Chem. Soc. Rev. 1998, 27, 145-154.
15. Najime, R.; Pilard, S.; Vaultier, M. Tetrahedron Lett. 1992, 37, 5351-5354.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 1998. Details of the quantum chemical calculations (Gaussian archive entries) are available from E.-U.W. upon request.
17. Grimme, S. J. Chem. Phys. 2003, 118, 9095-9102.
18. Marshall, H.; Penninger, J.; Weyerstahl, P. Liebigs Ann. Chem. 1982, 1, 49-67.
19. Eshelby, J. J.; Parsons, J. P.; Sillars, N. C.; Crowley, P. J. J. Chem. Soc., Chem. Commun. 1995, 15, 1497-1498.
20. Fronza, G.; Fuganti, C.; Grasselli, P. Tetrahedron: Asymmetry 1993, 4, 1909-1916.
21. Barrett, A. G. M.; Head, J.; Smith, L. M.; Stock, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005-6018.