Aldol condensation of amide enolates with imines affords β-amino acid dialkylamides in both high yields and excellent threo diastereoselectivity; electronic factors seem to be of great importance for successful interaction.
References
1.
GaudemarM., Organomet. Chem. Rev. A, 1972, 8, 183; D. J. Hart and D.-Ch. Ha, Chem. Rev., 1989, 89, 1447.
2.
DardoizeF., and GaudemarM., Bull. Soc. Chim. Fr., 1974, 939; F. Dardoize and M. Gaudemar, Chem. Rev., 1976, 1561.
3.
StefanovskyY.N., and KurtevB. J., C. r. Acad. bulg. Sci., 1969, 22, 53.
4.
(a) StefanovskyY.N., and VitevaL. Z., Monatsh. Chem., 1981, 112, 125;(b) L.Z. Viteva and Y.N. Stefanovsky, Monatsh. Chem., 1982, 113, 181;(c) Y. Stefanovsky, Tz. Gospodova and L. Viteva, Tetrahedron, 1986, 42, 5335;(d) L. Viteva and Y. Stefanovsky, J. Chem. Res., 1990, (S) 232;(e) L.Z. Viteva, Tz Gospodova and Y.N. Stefanovsky, Tetrahedron, 1994, 50, 7193;(f) L. Viteva and Tz. Gospodova, J. Chem. Res., 1996, (S)166.
5.
PearsonR.G., J. Am. Chem. Soc., 1963, 85, 3533.
6.
MukaiyamaT., SuzukiH., and YamadaT., Chem. Lett., 1986, 915.
7.
ZimmermanH.E., and TraxlerM. D., J. Am. Chem. Soc., 1957, 79, 1920.
8.
EvansD.A., NelsonJ. V., and TaberT. R., Top. Stereochem., 1982, 13, 1.
9.
GoasdoueC., GoasdoueN., GaudemarM., and MladenovaM., J. Organomet. Chem., 1981, 208, 279; R. E. Ireland, R. H. Mueller and A. K. Willard, J. Am. Chem. Soc., 1976, 98, 2867.