Sc(OTf)3-catalysed allylations of hydrates of α-keto aldehydes and glyoxylates and activated aromatic aldehydes with allyltrimethylsilane in H2O–CH3CN were examined. α-Keto and α-ester homoallylic alcohols 3a–d and aromatic homoallylic alcohols 3e–f were obtained in good to excellent yields, depending on the reaction temperature and the ratio of H2O to CH3CN in co-solvent.
References
1.
LiC.J., and ChanT. H.Organic Reactions in Aqueous Media, John Wiley & Sons, New York, 1997; For a review, see Li, C.J. Chem Rev., 1993, 93, 2023.
2.
KobayashiS., Lanthanides: Chemistry and Use in Organic synthesis, Springer, Berlin, 1999, and references cited therein.
3.
KobayashiS., HachiyaI., ArakiM., and IshitaniH., Tetrahedron Lett., 1993, 3755.
4.
KobayashiS., and IshitainiH., Chem. Common., 1995, 1329.
5.
KobayashiS., and HachiyaI., J. Org. Chem., 1994, 59, 3590.
6.
HachiyaI., and KobayashiS., J. Org. Chem., 1993, 58, 6958.
7.
AkiyamaT., IwaiJ., and SuganoM., Tetrahedron, 1999, 55, 7499.
8.
HosomiA., and SakuraiH., Tetrahedron Lett., 1976, 17, 1295.
9.
YangY., WangM. W., and WangD., Chem. Commun., 1997, 1651.
10.
For a review see: KobayashiS., Eur. J. Org. Chem.1999, 15.
11.
AggraualV.K., and VennallG. P., Synthesis, 1998, 1822.
12.
ChanT.H., and FlemingI., Synthesis, 1979, 761
13.
WhitesellJ.K., Acc. Chem. Res, 1985. 18, 280; P.H. Grossen, P. Mohr and C. Tamm, Helv. Chim. Acta, 1984, 67, 1625; K. Mikami and T. Nakai, J. Org. Chem., 1991, 56, 2952.
14.
WangD., WangZ. G., WangM. W., ChenY. J., LiuL., and ZhuY., Tetrahedron: Asymmetry, 1999, 10, 327.
15.
TakuwaA., NishigaichiY., YamashitaK., and IwamatoH., Chem. Lett., 1990, 1761.
16.
DavisA.P., and JasparsM., J. Chem Soc. Perkin Trans, 1992, I, 2111.