Effects of metal cations in Lewis acid-surfactant combined catalyst- mediated aldol reactions in water

Synlett

Volumn , Issue 5, 1999, Pages 547-548

  Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldol reaction; Lewis acid; Metal cation; Surfactant; Thioketene silyl acetal

Indexed keywords

ACID; METAL ION; SILANE DERIVATIVE; SURFACTANT; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HYDROLYSIS; REACTION ANALYSIS; REACTION TIME;

EID: 0032937845     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2685     Document Type: Article

References (11)

1. Organic Synthesis in Water; Grieco, P. A., Ed.; Blacky Academic and Professional: London, 1998.
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5. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.
6. Kobayashi, S.; Wakabayashi, T.; Nagayama, S.; Oyamada, H. Tetrahedron Lett. 1997, 38, 4559.
7. Kobayashi, S.; Wakabayashi, T. Tetrahedron Lett. 1998, 39, 5389.
8. Recently, Diels-Alder reactions catalyzed by copper bis(dodecyl sulfate) in water were reported: Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1998, 120, 9517.
9. Moroi, Y.; Motomura, K.; Matsuura, R. J. Colloid Interface Sci. 1974, 10, 3455.
10. 2,7-Dimethylnaphthalene (ca. 5 mol%) was used as an internal standard. A typical experimental procedure for Lewis acid-surfactant combined catalyst-mediated aldol reactions is as follows: To a mixture of 2,7-dimethylnaphthalene (ca. 5 mol%) and benzaldehyde (0.25 mmol, 1 eq) were added a Lewis acid-surfactant combined catalyst (10 mol%) and water (1.5 mL). After 10 min at 30 °C, thioketene silyl acetal 3 (1.5 eq) was added. The reaction mixture was stirred at 30 °C and monitored by GC.
11. 7 The critical micelle concentration of 1b is 1.2 mM at 30 °C. See: Satake, I.; Iwamatsu, I.; Hosokawa, S.; Matuura, R. Bull. Chem. Soc. Jpn. 1963, 36, 204.