α-Amidoalkylation reaction is a powerful tool of modern organic synthesis for carbon-carbon or
carbon-heteroatom bond formation. The distinguishing features of amidoalkylating reagents are
higher electrophilicity and wider structural diversity compared with those of reagents involved in
aminoalkylation reactions. Therefore, amidoalkylation has been extensively applied in the synthesis
of various nitrogencontaining acyclic and heterocyclic compounds including bioactive natural
products (e.g., alkaloids, antibiotics, toxins, vitamins) and pharmaceuticals. Recently, some
enantioselective variants of this reaction employing catalytic amounts of chiral auxiliaries has also
been described.
Download PDF
References
- Speckamp, W. and Roy, R.J, Netherlands Chem. Soc.,100, 345 (1981)
- Mollov, N.A. and Venkov, A., Symposium papers - IUPAC Int. Symp., Chem. Nat. Prod., 11th, 1978, 4 (Part 2), 280-292; C.A., 92, 6761 (1980).
- Kost, A., Suminov, S. and Sheinkman, Adv. Org. Chem. I., Part 2, 573 (1979).
- McEwen, W. and Cobb, R., Chem. Rev., 55, 511 (1955).
- Toshima, N., Asao, S., Takada, K., and Hirai, H., Tetrahedron Lett., 5123 (1970).
- Beak, P., and Reitz, D., Chem. Rev., 78, 275 (1978).
- Tramontini, M., Synthesis, 703 (1973).
- Ben-Ishai, D., Sataty, I., and Bernstein, Z., Tetrahedron, 32, 1571 (1976).
- Ben-Ishai, D., Moshenberg, R. and Altman, J., Tetrahedron, 33, 1533 (1977).
- Bott, K., Chem. Ber., 106, 2513 (1973).
- Danishefsky, S., Guingant, A., and Prisbylla, M., Tetrahedron Lett., 21, 2033 (1980).
- Kametani, T. et.al. Heterocycles, 12, 523 (1979).
- Yoshioka, T. et.al., Nippon Kagaku Kuishi, 860 (1981); Chem. Abstr., 95, 150285 (1981).
- Feiner, I. et.al., Angew. Chem., 79, 863 (1967).
- Ufer, G., Tjoa, S., and MacDonald, S., Can. J. Chem., 56, 2437 (1978).
- Shono, T., Matsumura, Y., Tsubata, K., and Takata, J., Chem. Lett., 1121 (1981).
- Kraus, G., and Neuenschwander, K., Tetrahedron Lett., 21, 3841 (1980)
- Stokker, G. et.al., J. Med. Chem., 23, 1414 (1980).
- Mitchell, A., Kent, S., Engelhard, M., and Marrifield, R., J. Org. Chem., 43, 2845 (1978)
- Guise, G., and Buhler, A., Text. Res. J., 47, 496 (1977).
- Nordeen, C., Abott Laboratories, unpublished work.
- Petersen, H., Synthesis, 243 (1973).
- Hellmann, and Optiz, a-Aminoalkylierung, Verlag, Chemie, GMBH, Weinheim, 64-79 (1960).
- Magat, Faris, and Salisbury, J. Amer. Chem. Soc., 73, 1028 (1951)
- Parris, and Christerson, J. Org. Chem., 25, 1888 (1968).
- Mowry and Ringwald, J. Amer. Chem. Soc., 72, 4439 (1950)
- Pandey, V.K., Acta Ciencia Indica, 4, 230-235 (1978).
- Pandey, V.K., Curr. Sci., 50, 678-80 (1981).
- Diesbach, Helv. Chim. Acta., 23, 1232 (1940)
- Tawney, Synder, Leibbrand Shteler and Williams, J. Org. Chem., 28, 15 (1961)
- Biltz, H., and Lachmann, F., J. Prakt. Chem., 113, 309 (1926).
- Oda, Teramura, Tenimoto, Suda, and Matsuda, Bull. Inst. Chem. Res. Kyota Univ., 33, 119 (1965); Chem. Abstr., 51, 11355 (1957).
- Einhorn, and Mauermayer, Ann., 343, 284 (1905)
- Nenitzesen, and Dinuiseu, Rev. Chim. Acad. Rep. Poulaire Roumaine, 2, 47 (1964); Commun. Acad. Rep. Populaire Romane, 4, 45 (1954); Chem. Abstr., 50, 15445 (1956).
- Zaugg, H.E., unpublished data.
- Zaugg, H.E. and Schaefer, J. Org. Chem., 28, 2925 (1963).
- Fischer, and Nenitzescu, Ann., 443, 113 (1925).
- Ishidate, of M., Sekiya, M. and Yanaihana, N., Chem. Ber., 93, 2898 (1968).
- Nordeen, C., Abbott Laboratories, unpublished work
- Crowley, S., Abott Laboratories, unpublished work
- Anderson, P., J. Org. Chem., 44, 1519 (1979)
- Gale, D., and Wishire, J., Aus. J. Chem., 28, 2447 (1975)
- Barry, J., Mayeda, E., and Roso, S., Tetrahedron, 33, 309 (1977)
- Schaeffer, W., U.S. Patent, 3190882 (1962); Chem. Abstr., 63, 9821, 1965
- Nyberg, K., Acta. Chem. Scand., 28, 825 (1974).
- Hess, F., Cullen, E., and Grozinger, K., Tetrahedron Lett., 2591 (1971).
- Menti, L., Gazz. Chim. Scand., 28, 825 (1974).
- Hess, F., and Stenwart, P., J. Med. Chem., 18, 320 (1975).
- Ben-Ishai, D., Altman, J., and Peled, N., Tetrahedron, 33, 2715 (1977).
- Ben-Ishai, D., and Bernstein, Z., Tetrahedron, 33, 3261 (1977).
Back