Ln(OTf)3- or Cu(OTf)2-catalyzed Mannich-type reactions of aldehydes, amines, and silyl enolates in micellar systems. Facile synthesis of β-amino ketones and esters in water

Synlett

Volumn , Issue 5, 1999, Pages 545-546

  Kobayashi, Shu ^a   Busujima, Tsuyoshi ^a   Nagayama, Satoshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aqueous reaction; Benign chemical synthesis; Lanthanide triflate; Mannich reaction; Micellar system

Indexed keywords

ALDEHYDE DERIVATIVE; AMINE; ESTER DERIVATIVE; KETONE DERIVATIVE; SILANE DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROPHOBICITY; MICELLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032946766     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2693     Document Type: Article

References (26)

1. (a) Grieco, P. Ed. Organic Reactions in Water, Chapman & Hall, 1998.
2. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media, Wiley: New York, 1997.
3. (c) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741.
4. (d) Li, C.-J. Chem. Rev. 1993, 93, 2023.
5. (e) Reissig, H.-U. In Organic Synthesis Highlights, Waldmann, H. Ed. VCH: Weinheim, 1991, p 71.
6. (f) Einhorn, C.; Einhorn, J. Synthesis 1989, 787.
7. (a) Kobayashi, S. Chem. Lett. 1991, 2187.
8. (b) Kobayashi, S. Synlett 1994, 689.
9. (c) Kobayashi, S. Organic Reactions in Water, Grieco, P. Ed. Chapman & Hall, 1998, p. 262.
10. (d) Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
11. Kobayashi, S.; Wakabayashi, T.; Nagayama, S.; Oyamada, H. Tetrahedron Lett. 1997, 38, 4559. See also, Kobayashi, S.; Wakabayashi, T.; Oyamada, H. Chem. Lett. 1997, 831.
12. Kobayashi, S.; Wakabayashi, T.; Nagayama, S.; Oyamada, H. Tetrahedron Lett. 1997, 38, 4559. See also, Kobayashi, S.; Wakabayashi, T.; Oyamada, H. Chem. Lett. 1997, 831.
13. Kleinnmann, E. F. In Comprehensive Organic Synthesis Trost, B. M. Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 4.1.
14. (a) Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 36, 5773.
15. (b) Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. J. Org. Chem. 1996, 61, 8293.
16. For aqueous Mannich-type reactions, (a) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
17. (b) Loh, T.-P; Wei, L.-L. Tetrahedron Lett. 1998, 39, 323.
18. We have recently developed three-component coupling reactions of aldehydes, amines, and allyltributyltin in micellar systems. Kobayashi, S.; Busujima, T.; Nagayama, S. J. Chem. Soc., Chem. Commun. 1998, 19. It is noted that silyl enolates are much easier to hydrolyze than allyltributyltin in water. See also, Kobayashi, S.; Busujima, T.; Nagayama, S. J. Chem. Soc., Chem. Commun. 1998, 981.
19. We have recently developed three-component coupling reactions of aldehydes, amines, and allyltributyltin in micellar systems. Kobayashi, S.; Busujima, T.; Nagayama, S. J. Chem. Soc., Chem. Commun. 1998, 19. It is noted that silyl enolates are much easier to hydrolyze than allyltributyltin in water. See also, Kobayashi, S.; Busujima, T.; Nagayama, S. J. Chem. Soc., Chem. Commun. 1998, 981.
20. 1 the mixture was diluted with water and ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was dried, filtered, and concentrated. The crude adduct was purified by column chromatography on silica gel to afford the pure desired β-amino carbonyl compound.
21. Only a trace amount of the product was obtained without SDS under the same reaction conditions.
22. Similar reactions performed in organic solvents sometimes induced certain amounts of deamination products.
23. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.
24. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
25. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
26. Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049.