Bismuth Trichloride as a New Efficient Catalyst in the Aldol Reaction and the Michael Reaction

In the presence of a catalytic amount of bismuth(III) trichloride (5 mol%), silyl enol ethers react with aldehydes at room temperature in dichloromethane to give the corresponding aldols in good yields. Silyl enol ethers also have been found to react with α,β-unsaturated ketones at room temperature in dichloromethane to afford the corresponding 1,5-dicarbonyl compounds, the Michael adducts in good yields. The intermediate adducts of the aldol reaction (the silyl ethers) and the Michael reaction (the silyl enol ethers) were also obtained in good yields.

[1]  K. Akiba,et al.  A grignard-type addition of allyl unit to aldehydes by using bismuth and bismuth salt , 1990 .

[2]  L. D. Freedman,et al.  Bismuth annual survey covering the year 1988 , 1990 .

[3]  J. Finet.  Arylation reactions with organobismuth reagents , 1989 .

[4]  H. Ohki,et al.  Organic Synthesis Using Bismuth and Bismuth Compounds , 1989 .

[5]  L. D. Freedman,et al.  Bismuth Annual survey covering the year 1987 , 1989 .

[6]  K. Akiba,et al.  Bismuth trichloride as a new efficient catalyst in the aldol reaction , 1988 .

[7]  D. Barton,et al.  Bismuth(V) reagents in organic synthesis , 1987 .

[8]  Y. Izumi,et al.  Aldol-type reactions between trimethylsilyl enol ethers and acetals with the aid of rhodium complex , 1987 .

[9]  M. Reetz,et al.  Rhodium-diphosphine complexes as catalysts in aldol additions , 1987 .

[10]  Y. Izumi,et al.  The first example of aldol reactions between trimethylsilyl enol ethers and aldehydes by the aid of rhodium complex , 1986 .

[11]  K. Akiba,et al.  Carbon-carbon bond formation with bismuth salt: a chemoselective Grignard-type addition of allyl unit to aldehydes , 1986 .

[12]  Isao Kuwajima,et al.  Reactive enolates from enol silyl ethers , 1985 .

[13]  K. Akiba,et al.  Metallic bismuth mediated allylation of aldehydes to homoallylic alcohols , 1985 .

[14]  R. Noyori,et al.  Tris(dialkylamino)sulfonium enolates. Synthesis, structure, and reactions , 1983 .

[15]  R. Noyori,et al.  Trialkylsilyl triflates. 5. A stereoselective aldol-type condensation of enol silyl ethers and acetals catalyzed by trimethylsilyl trifluoromethanesulfonate , 1980 .

[16]  J. E. Sohn,et al.  Acyclic stereoselection. 7. Stereoselective synthesis of 2-alkyl-3-hydroxy carbonyl compounds by aldol condensation , 1980 .

[17]  K. Narasaka.  Cross Aldol Reaction , 1979 .

[18]  T. Mukaiyama.  Titanium Tetrachloride in Organic Synthesis [New synthetic methods (21)] , 1977 .

[19]  I. Kuwajima,et al.  Fluoride ion catalyzed aldol reaction between enol silyl ethers and carbonyl compounds , 1977 .

[20]  Kazuo Banno,et al.  New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride , 1974 .

[21]  H. O. House,et al.  Chemistry of carbanions. XVIII. Preparation of trimethylsilyl enol ethers , 1969 .