Aza-Michael addition of chiral hydrazines to alkylidene malonates

Tetrahedron

Volumn 61, Issue 19, 2005, Pages 4609-4613

  Prieto, Auxiliadora ^a   Fernández, Rosario ^a   Lassaletta, José M ^b   Vázquez, Juan ^a   Alvarez, Eleuterio ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

Conjugate addition; Hydrazines; Synthetic methods

Indexed keywords

ALKENE DERIVATIVE; ALKYL GROUP; HETEROCYCLIC COMPOUND; HYDRAZINE DERIVATIVE; MALONIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHIRALITY; MICHAEL ADDITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 17144414831     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.006     Document Type: Article

References (30)

1. E. Juaristi Enantioselective Synthesis of β-Amino Acids 1997 Wiley New York
2. M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991
3. D. Enders, S. Müller, and G. Raabe Angew. Chem., Int. Ed. 38 1999 195
4. D. Enders, S. Müller, and G. Raabe Eur. J. Org. Chem. 2000 879
5. D. Enders, and S. Wallert Synlett 2002 304
6. D. Enders, and S. Wallert Tetrahedron Lett. 43 2002 5109
7. D. Enders, W. Heiner, and W. Bettray Angew. Chem., Int. Ed. Engl. 34 1995 455
8. K. Voigt, A. Lansky, M. Noltemeyer, and A. de Meijere Liebigs Ann. 1996 899
9. D. Enders, J. Wiedemann, and W. Bettray Synlett 1995 369
10. D. Enders, and J. Wiedemann Liebigs Ann./Recueil 1997 699
11. J.M. Lassaletta, J. Vázquez, A. Prieto, R. Fernández, G. Raabe, and D. Enders J. Org. Chem. 68 2003 2698
12. G. Cardillo, L. Gentilucci, M. Gianotti, H. Kim, R. Perciaccante, and A. Tolomelli Tetrahedron: Asymmetry 12 2001 2395
13. G. Cardillo, S. Fabbroni, L. Gentilucci, M. Gianotti, R. Perciaccante, and A. Tolomelli Tetrahedron: Asymmetry 13 2002 1407
14. L. Tedeschi, and D. Enders Org. Lett. 3 2001 3515
15. D.A. Evans, T. Rovis, M.C. Kozlowski, and J.S. Tedrow J. Am. Chem. Soc. 121 1999 1994
16. D.A. Evans, T. Rovis, M.C. Kozlowski, C.W. Downey, and J.S. Tedrow J. Am. Chem. Soc. 122 2000 9134
17. S.J. Blarer, and D. Seebach Chem. Ber. 116 1983 2250
18. J. Martens, and S. Lübben Tetrahedron 47 1991 1205 Recently, a related Friedel-Crafts addition of several aromatic heterocycles has also been reported:
19. W. Zhuang, T. Hansen, and K.A. Jørgensen Chem. Commun. 2001 347
20. J.M. Betancort, K. Sakthivel, R. Thayumanavan, and C.F. Barbas III Tetrahedron Lett. 42 2001 4441
21. H. Stetter, and F. Jonas Chem. Ber. 114 1981 564
22. H. Cerfontain, and P.C.M. van Noort Synthesis 1980 490
23. D. Enders, and J. Wiedemann Synthesis 1996 1443
24. S.J. Blarer, and D. Seebach Chem. Ber. 116 1983 2250
25. W.N. Olmstead, and F.J. Bordwell J. Org. Chem. 45 1980 3299
26. K. Toni, and M. Shing Tetrahedron 44 1988 7261
27. D. Enders, H. Kipphardt, P. Gerdes, L.J. Breña-Valle, and V. Buhshan Bull. Soc. Chim. Belg. 97 1988 691
28. M. Alcarazo, J. Stephen, E. Alonso, R. Fernández, E. Álvarez, F. Lahoz, and J.M. Lassaletta J. Am. Chem. Soc. 126 2004 13242
29. J.M. Lassaletta, M. Alcarazo, and R. Fernández Chem. Commun. 3 2004 298
30. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 257697. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].