Synthesis of β-amino esters via aza-Michael addition of amines to alkenes promoted on silica: A useful and recyclable surface

Synlett

Volumn , Issue 14, 2004, Pages 2630-2632

  Basu, Basudeb ^a   Das, Pralay ^a   Hossain, Ismail ^a  

^a UNIVERSITY OF NORTH BENGAL   (India)

Author keywords

amino esters; Amines; Aza Michael addition; Conjugated alkenes; Silica gel

Indexed keywords

ALIPHATIC AMINE; ALKENE DERIVATIVE; AMINE; AROMATIC AMIDE; BETA AMINO ACID; ESTER; HETEROCYCLIC COMPOUND; NITRILE; SILICA GEL; SILICON DIOXIDE;

ARTICLE; COLUMN CHROMATOGRAPHY; CONJUGATE; MICHAEL ADDITION; RECYCLING; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 9644302416     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834836     Document Type: Article

References (28)

1. (a) Frackenpohl, J.; Arvidsson, P. I.; Schreiber, J. V.; Seebach, D. ChemBioChem 2001, 2, 445.
2. (b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
3. (c) Nicolaou, K. C.; Dai, V.-M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
4. Hayashi, Y.; Katada, J.; Harada, T.; Tachiki, A.; Ijima, K.; Takiguchi, Y.; Muramatsu, M.; Miyazaki, H.; Asari, T.; Okazaki, T.; Sato, Y.; Yasuda, E.; Yano, M.; Uno, I.; Ojima, I. J. Med. Chem. 1998, 41, 2345.
5. (a) Texier-Boullet, F.; Latouche, R.; Hamelin, J. Tetrahedron Lett. 1993, 34, 2123.
6. (b) Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287.
7. (c) Salzman, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Boufford, F. A. J. Am. Chem. Soc. 1980, 702, 6161.
8. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995.
9. (a) Ben Ayed, T.; Amiri, H.; El Gaied, M. M.; Villieras, J. Tetrahedron 1995, 51, 9633.
10. (b) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
11. (c) Bull, S. D.; Davies, S. G.; Delgado-Ballester, S.; Fenton, G.; Kelly, P. M.; Smith, A. D. Synlett 2000, 1257.
12. (d) Davies, S. G.; McCarthy, T. D. Synlett 1995, 700.
13. (e) Rosenthal, D.; Braundrup, G.; Davies, K. H.; Wall, M. E. J. Org. Chem. 1965, 30, 3689.
14. (a) Jenner, G. Tetrahedron Lett. 1995, 36, 233.
15. (b) Matsubara, S.; Yoshiyoka, M.; Utimoto, K. Chem. Lett. 1994, 827.
16. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 720; and references cited therein.
17. Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109.
18. Bartoli, G.; Bosco, M.; Marcantoni, E.; Petrini, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052; and references cited therein.
19. Shaikh, N. S.; Deshpande, V. H.; Bedekar, A. V. Tetrahedron 2001, 57, 9045.
20. (a) Cave, G. W. V.; Raston, C. L.; Scott, J. L. Chem. Commun. 2001, 2159.
21. (b) Tanaka, K.; Toda, F. Chem. Rev. 2000, 700, 1025.
22. (c) Metzger, J. O. Angew. Chem. Int. Ed. 1998, 37, 2975.
23. Ranu, B. C.; Dey, S. S.; Hajra, A. Arkivoc 2002, 7, 75.
24. (a) Basu, B.; Jha, S.; Mridha, N. K.; Bhuiyan, M. M. H. Tetrahedron Lett. 2002, 43, 7967.
25. (b) Basu, B.; Das, P.; Bhuiyan, M. M. H.; Jha, S. Tetrahedron Lett. 2003, 44, 3817.
26. (c) Das, P.; Basu, B. Synth. Commun. 2004, 34, 2184.
27. 13C NMR spectral data.
28. 13C NMR: δ = 14.1, 32.5, 34.7, 50.9, 53.1, 60.3, 64.1, 106.9, 172.5.