Efficient cross-aldol condensation of cyclopentanone, cyclohexanone and 1-indanone with various aromatic aldehydes is catalysed with TiCl3(SO3CF3) at room temperature in excellent yields.
References
1.
DeliJ., LorandT., SzaboD. and FoldesiA., Pharmazie, 1984, 39, 539.
2.
NielsenA. T. and HoulihanW., J. Org. React., 1968, 16, 1;
3.
MurrayR. J.CromwellN. H., J. Org. Chem., 1976, 41, 3540; (c) SinisterraJ. V. and Garcia-RasoA., Synthesis, 1984, 502; (d)
4.
ReevesR. L., Chemistry of Carbonyl Group, ed. PataiS., Wiley-Interscience, New York, 1966, p. 580.
5.
IwataM. and EmotoS., Bull. Chem. Soc. Jpn., 1976, 49, 1369.
6.
IrieK. and WatanabeK. I., Bull. Chem. Soc. Jpn, 1980, 53, 1366.
7.
KelleherR. G., McKerveyM. A. and VibuljanP. J., J. Chem. Soc., Chem. Commun., 1980, 486.
8.
WatanabeK. I. and ImazawaA., Bull. Chem. Soc. Jpn., 1982, 55, 3208.
9.
ChuitC., CorriuR. T. P., ReyeC., Synthesis, 1983, 294; MahrwaldR. and SchickH., Synthesis, 1990, 593.
10.
NakamoT., IrifuneS., UmanoS., InadaA., IshiiY. and OgawaM., J. Org. Chem., 1987, 52, 2239.
11.
ZehengM., WangL., ShaoJ. and ZhongQ., Synth. Commun., 1997, 27, 351.
12.
IranpoorN. and KazemiF., Tetrahedron, 1998, 54, 9475.
13.
IranpoorN. and ZeynizadehB., J. Chem. Res., 1998, 466; Synlett, 1998, 1079.
14.
NoftleR. and CadyG. H., Inorg. Chem., 1966, 5, 2182.
15.
GarlanC. E. and ReidE. Emmet, J. Am. Chem. Soc., 1925, 47, 2335;
16.
MaccioniA. and MarongiuE., Ann. Chim. (Rome), 1958, 48, 557; Chem. Abstr., 1959, 53, 5227i;
17.
Buu-HoiN. P. and XoungN. D., Bull. Soc Chim. Fr., 1958, 758.
18.
HuitricA. C. and KulmlerW. D., J. Am. Chem. Soc., 1956, 78, 614.
19.
KevillD. N., WeilerE. D. and CromwellN. H., J. Org. Chem., 1964, 29, 1276.
20.
KevillD. N., WeilerE. D. and CromwellN. H., J. Am. Chem. Soc., 1966, 88, 4489.
21.
Buu-HoiN. P. and XoungN. D., J. Chem. Soc., 1952, 2225.
22.
CoppensG. A., CoppensM., KevillD. N. and CromwellN. H., J. Org. Chem., 1963, 28, 3267.