A Bronsted acid-surfactant-combined catalyst for Mannich-type reactions of aldehydes, amines, and silyl enolates in water

Synlett

Volumn , Issue 9, 1999, Pages 1401-1402

  Manabe, Kei ^a   Mori, Yuichiro ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Bronsted acid; Mannich reaction; Silyl enolate; Sulfonic acid; Surfactant

Indexed keywords

ALDEHYDE; AMINE; SILYLENOLATE; SURFACTANT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; HYDROPHOBICITY; SYNTHESIS;

EID: 0032850169     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2871     Document Type: Article

References (14)

1. (a) Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998.
2. (b) Li, C.-J. Chem. Rev. 1993, 93, 2023.
3. (a) Kobayashi, S. Lanthanides: Chemistry and Use in Organic Synthesis; Springer: Heidelberg, 1999, p.63.
4. (b) Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
5. (c) Kobayashi, S. Synlett 1994, 689.
6. Kobayashi, S.; Wakabayashi, T. Tetrahedron Lett. 1998, 39, 5389.
7. Manabe, K.; Kobayashi, S. Synlett 1999, 547.
8. Kleinnmann, E. F. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: New York, 1991; Vol. Vol. 2, Chapter 4.1.
9. Kobayashi, S.; Busujima, T.; Nagayama, S. Synlett 1999, 545.
10. Unpublished.
11. Manabe, K.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3773.
12. 2O in the presence of SDS. See the preceding paper. Cf. Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett in press.
13. Dodecylbenzenesulfonic acid (soft type) was purchased from Tokyo Kasei Kogyo Co., Ltd., and used without further purification. This is a mixture of several linear alkylbenzenesulfonic acids. Its molecular weight was regarded as 326.50.
14. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 10049.