Iron(III) chloride as a water-compatible lewis acid for diastereoselective aldol reactions in water in the presence of a surfactant

Chemistry Letters

Volumn 33, Issue 3, 2004, Pages 312-313

  Aoyama, Naohiro ^a   Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; FERROUS CHLORIDE; LEWIS ACID; SILICON; SURFACTANT; WATER;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; EPIMERIZATION; STEREOCHEMISTRY;

EID: 2442665167     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.312     Document Type: Article

References (17)

1. For review, see: C.-J. Li and T.-H. Chan, "Organic Reactions in Aqueous Media," John Wiley & Sons, New York (1997); P. A. Grieco "Organic Synthesis in Water," Blackie Academic and Professional, London (1998); S. Kobayashi and K. Manabe, Acc. Chem. Res., 35, 209 (2002).
2. For review, see: C.-J. Li and T.-H. Chan, "Organic Reactions in Aqueous Media," John Wiley & Sons, New York (1997); P. A. Grieco "Organic Synthesis in Water," Blackie Academic and Professional, London (1998); S. Kobayashi and K. Manabe, Acc. Chem. Res., 35, 209 (2002).
3. For review, see: C.-J. Li and T.-H. Chan, "Organic Reactions in Aqueous Media," John Wiley & Sons, New York (1997); P. A. Grieco "Organic Synthesis in Water," Blackie Academic and Professional, London (1998); S. Kobayashi and K. Manabe, Acc. Chem. Res., 35, 209 (2002).
4. 3, see: K. Manabe, Y. Mori, T. Wakabayashi, S. Nagayama, and S. Kobayashi, J. Am. Chem. Soc., 122, 7202 (2000); S. Kobayashi and T. Wakabayashi, Tetrahedron Lett., 39, 5389 (1998); For other Lewis acid-surfactant-combined catalysts, see: K. Manabe, Y. Mori, and S. Kobayashi, Tetrahedron, 55. 11203 (1999); K. Manabe and S. Kobayashi, Synlett, 1999, 547.
5. 3, see: K. Manabe, Y. Mori, T. Wakabayashi, S. Nagayama, and S. Kobayashi, J. Am. Chem. Soc., 122, 7202 (2000); S. Kobayashi and T. Wakabayashi, Tetrahedron Lett., 39, 5389 (1998); For other Lewis acid-surfactant-combined catalysts, see: K. Manabe, Y. Mori, and S. Kobayashi, Tetrahedron, 55. 11203 (1999); K. Manabe and S. Kobayashi, Synlett, 1999, 547.
6. 3, see: K. Manabe, Y. Mori, T. Wakabayashi, S. Nagayama, and S. Kobayashi, J. Am. Chem. Soc., 122, 7202 (2000); S. Kobayashi and T. Wakabayashi, Tetrahedron Lett., 39, 5389 (1998); For other Lewis acid-surfactant-combined catalysts, see: K. Manabe, Y. Mori, and S. Kobayashi, Tetrahedron, 55. 11203 (1999); K. Manabe and S. Kobayashi, Synlett, 1999, 547.
7. 3, see: K. Manabe, Y. Mori, T. Wakabayashi, S. Nagayama, and S. Kobayashi, J. Am. Chem. Soc., 122, 7202 (2000); S. Kobayashi and T. Wakabayashi, Tetrahedron Lett., 39, 5389 (1998); For other Lewis acid-surfactant-combined catalysts, see: K. Manabe, Y. Mori, and S. Kobayashi, Tetrahedron, 55. 11203 (1999); K. Manabe and S. Kobayashi, Synlett, 1999, 547.
8. S. Kobayashi, T. Wakabayashi, and H. Oyamada, Chem. Lett., 1997, 831.
9. Y. Mori, K. Kakumoto, K. Manabe, and S. Kobayashi, Tetrahedron Lett., 41, 3107 (2000).
10. 2+ salts are water-compatible Lewis acids. S. Kobayashi, S. Nagayama, and T. Busujima, J. Am. Chem. Soc., 120, 8287 (1998).
11. We like to use this system to evaluate Lewis acid catalysis in water because decomposition (hydrolysis) of silicon enolates is competitive to the desired aldol reactions.
12. 3 (20 mol %) gave only 21 % yield. See Ref. 5.
13. For our recent examples of diastereoselective aldol reactions in water, see: Y. Mori, K. Manabe, and S. Kobayashi, Angew. Chem., Int. Ed., 40, 2816 (2001); Y. Mori, J. Kobayashi, K. Manabe, and S. Kobayashi, Tetrahedron, 58, 8263 (2002).
14. For our recent examples of diastereoselective aldol reactions in water, see: Y. Mori, K. Manabe, and S. Kobayashi, Angew. Chem., Int. Ed., 40, 2816 (2001); Y. Mori, J. Kobayashi, K. Manabe, and S. Kobayashi, Tetrahedron, 58, 8263 (2002).
15. For review, see: E. P. Kündig and C. M. Saudan, in "Lewis acids in Organic Synthesis," ed. by H. Yamamoto, WILEY-VCH, Weinheim (2000), Vol. 2, Chap. 14, p 597.
16. O. Muñoz-Muñiz, M. Quintanar-Audelo, and E. Juaristi, J. Org. Chem., 68, 1622 (2003).
17. For an example, see: S. Yamago, D. Machii, and E. Nakamura, J. Org. Chem., 56, 2098 (1991).