Aziridination of 2-(phenylsulfinyl)-2-cycloakenones with arylsulfonyloxycarbamates

European Journal of Organic Chemistry

Volumn , Issue 23, 2002, Pages 4071-4074

  Fioravanti, Stefania ^a   Mascia, M Gabriella ^a   Morreale, Alberto ^a   Pellacani, Lucio ^a   Tardella, Paolo A ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Amination; Diastereoselectivity; Fused ring systems; Nitrogen heterocycles; Sulfoxides

Indexed keywords

ALKENE; AZIRIDINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; SULFOXIDE;

AMINATION; ARTICLE; BINDING AFFINITY; CHIRALITY; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0036898397     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200212)2002:23<4071::AID-EJOC4071>3.0.CO;2-V     Document Type: Article

References (26)

1. [1a] D. Tanner, Angew. Chem. 1994, 6, 625-646; Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
2. [1a] D. Tanner, Angew. Chem. 1994, 6, 625-646; Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
3. [1b] H. M. I. Osborn, J. Sweeney, Tetrahedron: Asymmetry 1997, 8, 1693-1715.
4. [1c] A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372.
5. [1d] H. Stamm, J. Prakt. Chem. 1999, 4, 319-331.
6. [1e] R. S. Atkinson, Tetrahedron 1999, 55, 1519-1559.
7. [1f] R. H. Dodd, Molecules 2000, 5, 293-298.
8. [1g] W. McCoull, F. A. Davis, Synthesis 2000, 1347-1365.
9. [1h] T. Siu, A. K. Yudin, J. Am. Chem. Soc. 2002, 124, 530-531.
10. [1i] J. B. Sweeney, Chem. Soc. Rev. 2002, 31, 247-258.
11. S. Fioravanti, L. Pellacani, S. Stabile, P. A. Tardella, R. Ballini, Tetrahedron 1998, 54, 6169-6176.
12. S. Fioravanti, A. Morreale, L. Pellacani, P. A. Tardella, Synthesis 2001, 1975-1978.
13. S. Fioravanti, A. Morreale, L. Pellacani, P. A. Tardella, J. Org. Chem. 2002, 67, 4972-4974.
14. M. C. Carreño, Chem. Rev. 1995, 95, 1717-1760.
15. M. C. Carreño, E. Dominguez, J. L. Garcia Ruano, C. Pedregal, J. H. Rodriguez, Tetrahedron 1991, 47, 10035-10044.
16. J. L. G. Ruano, I. Fernandez, C. Hamdouchi, Tetrahedron Lett. 1995, 36, 295-298.
17. J. L. G. Kuano, I. Fernandez, M. D. P. Catalina, A. A. Cruz, Tetrahedron: Asymmetry 1996, 7, 3407-3414.
18. F. A. Davis, P. Zhou, C. H. Liang, R. E. Reddy, Tetrahedron: Asymmetry 1995, 6, 1511-1514.
19. G. H. Posner, Acc. Chem. Res. 1987, 20, 72-78.
20. G. Rothenberg, A. P. Downie, C. L. Raston, J. L. Scott, J. Am. Chem. Soc. 2001, 123, 8701-8708.
21. S. Fioravanti, L. Pellacani, P. A. Tardella, Gazz. Chim. Ital. 1997, 127, 41-44 and refs. therein, and our other unpublished results.
22. S. Hanessian, S. Johnstone, J. Org. Chem. 1999, 64, 5896-5903.
23. T. Yechezkel, E. Ghera, D. Ostercamp, A. Hassner, J. Org. Chem. 1995, 60, 5135-5142.
24. W. Lwowski, T J. Maricich, J. Am. Chem. Soc. 1965, 87, 3630-3637.
25. M. R. Banks, J. I. G. Cadogan, I. Gosney, P. K. G. Hodgson, P. R. R. Langridge-Smith, J. R. A. Millar, A. T. Taylor, J. Chem. Soc., Chem. Commun. 1995, 885-886.
26. C. Greck, L. Bischoff, A. Girard, J. Hajicek, J. P. Genêt, Bull. Soc. Chim. Fr. 1994, 131, 429-433.