Acidic clay catalyzed reaction of malononitrile derivatives with an excess of 1,2-aminoalcohol furnishes mono-oxazolines selectively; a simple strategy to prepare 2,2-dialkyl-3-aminopropionic acid derivatives is presented.
References
1.
LaszloP., Science, 1987, 235, 1473; Pure Appl. Chem., 1990, 62, 2027; A. Cornelis and P. Laszlo, Synlett., 1994, 155.
2.
JnaneshwaraG. K., DeshpandeV. H., LalithambikaM., RavindranathanT., and BedekarA. V., Tetrahedron Lett., 1998, 39, 459.
3.
FrumpJ. A., Chem. Rev., 1971, 71, 483; T. W. Greene and P. G. M. Wuts, in Protecting Groups in Organic Synthesis, J. Wiley, New York, 2nd edn., 1991; P. J. Kocienski, in Protecting Groups, ed. EndersD., NoyoriR., and TrostB. M., George Thieme, Verlag, Stuttgart, New York, 1994.
4.
LutomskiK. A., and MeyersA. I., in Asymmetric Synthesis, ed. MorissonJ. D., Academic Press, Orlando, FL, 1984, vol. 3, pp. 213; A. I. Meyers, Acc. Chem. Res., 1978, 11, 375; A. I. Meyers and E. D. Mihelich, Angew. Chem., Int. Ed. Engl., 1978, 15, 270; M. Reuman and A. I. Meyers, Tetrahedron, 1985, 41, 837; T. G. Gant and A. I. Meyers, Tetrahedron, 1994, 50, 2297; A. Pfaltz, Acc. Chem. Res., 1993, 26, 339; Acta Chem. Scand., 1996, 50, 189; A. K. Ghosh, P. Mathivanan and J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1.
5.
DaviesI. W., SenanayakeC. H., LarsenR. D., VerhoevenT. R, and ReiderP. J., Tetrahedron Lett., 1996, 37, 813.
6.
SmithM. B., in Methods of Non-α-amino acid Synthesis, M. Dekker, New York, 1995.
7.
TestaE., and FontanellaL., Br. Pat. 1962, 829663 (Chem. Abstr., 1962, 56, P1430c); B. J. R Nicolaus, E. Bellasio, G. Pagani and E. Testa, Gazz. Chim. Ital., 1963, 93, 618.