Indium-trichloride catalyzed Mukaiyama-aldol reaction in water: Solubility, aggregation and internal pressure effect

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3465-3468

  Loh, Teck Peng ^a   Pei, Jian ^a   Koh, Kevin Siong Ve ^a   Cao, Guo Qiang ^a   Li, Xu Ran ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

KETOL;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031027878     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00595-9     Document Type: Article

References (13)

1. (a) For pioneering work in organic reactions: Mukaiyama T.; Narasaka K.; Banno T. Chem. Lett. 1973, 1011.; Mukaiyama, T.; Banno, T.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
2. (a) For pioneering work in organic reactions: Mukaiyama T.; Narasaka K.; Banno T. Chem. Lett. 1973, 1011.; Mukaiyama, T.; Banno, T.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
3. (b) Water-promoted aldol reaction under pressure of silyl enol ethers with carbonyl compounds: Lubineau A. J.Org.Chem. 1986, 51, 2142: Lubineau A.; Meyer E. Tetrahedron. 1988, 44, 6065.
4. (b) Water-promoted aldol reaction under pressure of silyl enol ethers with carbonyl compounds: Lubineau A. J.Org.Chem. 1986, 51, 2142: Lubineau A.; Meyer E. Tetrahedron. 1988, 44, 6065.
5. (c) In aqueous reactions using Lanthanide triflates: Kobayashi S.; Hachiya I. J.Org.Chem. 1994, 59, 3590. Kobayashi S. Chem.Lett. 1991 2187.
6. (c) In aqueous reactions using Lanthanide triflates: Kobayashi S.; Hachiya I. J.Org.Chem. 1994, 59, 3590. Kobayashi S. Chem.Lett. 1991 2187.
7. (d) In pure water: Loh T.P.; Pei J.; Cao G.Q. J.Chem.Soc. Chem. Commun. 1996, 1819.
8. Personal communication.
9. 3 was recovered after purification of 98% from Aldrich.
10. (a) Franks F. 'In Watere, A Comprehensive Treatise'; Franks F., Ed; Plenum. N.Y. (1975).
11. (b). Tanford C., 'In The Hydrophobic Effect'. Wiley. N.Y. (1980).
12. (c) Breslow R., Rideout D.C. J. Am.Chem. Soc. 1980, 102, 7816.
13. (d) Grieco P.; Garner P.; He Z. Tetrahedron.Lett. 1983, 24, 1897.