Novel one-pot Mannich-type reaction in water: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 323-326

  Loh, Teck Peng ^a   Wei, Lin Li ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; BETA AMINO ACID; ETHER DERIVATIVE; KETONE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032518770     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10478-6     Document Type: Article

References (21)

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8. b) Loh, T.-P.; Wei, L.-L. Indium Trichloride Catalyzed Michael Reaction of Silyl Enol Ether under Neat Condition, submitted.
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20. 8. A typical reaction procedure is as follows: The solution of 38% formaldehyde solution (0.5 mmol, 37μL), aniline (0.5 mmol, 46 μL) in the presence of indium trichloride (22.1 mg, 0.1 mmol, 20 mol%) in water (5 rriL) was stirred for half an hour and then 1-phenyl-1-trimethylsiloxyethylene (192.3 mg, 1 mmol) was added. The resulting mixture was stirred at room temperature for 24 h. The product was extracted with ethyl acetate three times and the organic layers were combined and dried with anhydrous magnesium sulphate. The solvent was evaporated and the crude product was purified by silica gel colummn chromatography to afford the β-amino ketone in 91% yield (102.5 mg).
21. 9. These results are limited to non-enolizable imines. We have also investigated the alphatic enolizable imines derived from alkyl aldehydes (such as valeraldehyde) and found the yields were poor.