Abstract
Published data dealing with the synthesis of esters of β-amino acids by nucleophilic addition of amines and metal amides to esters of α,β-unsaturated carboxylic acids are considered. Information on the influence of various factors on the chemical yield and diastereoselectivity of the Michael reaction is discussed systematically. The bibliography includes 70 references.
References
1.
Rao V.S., Vasudevan T.K.
Critical Reviews in Biochemistry ,
1983
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
Hart D.J., Ha D.C.
Chemical Reviews ,
1989
4.
J. Brown M.
Heterocycles ,
1989
5.
van der Steen F.H., van Koten G.
Tetrahedron ,
1991
6.
Estermann H., Seebach D.
Helvetica Chimica Acta ,
1988
7.
Bovy P.R., Rico J.G.
Tetrahedron Letters ,
1993
8.
Perlmutter P., Tabone M.
Tetrahedron Letters ,
1988
9.
9
V. H. Lynch
Carnegie Inst. Year Book ,
1954
10.
Jenner G.
Tetrahedron Letters ,
1995
11.
FURUKAWA M., OKAWARA T., TERAWAKI Y.
Chemical and Pharmaceutical Bulletin ,
2011
12.
Kinas R., Pankiewicz K., Stec W.J., Farmer P.B., Foster A.B., Jarman M.
Journal of Organic Chemistry ,
1977
13.
Davies S.G., Ichihara O.
Tetrahedron Asymmetry ,
1991
14.
D'Angelo J., Maddaluno J.
Journal of the American Chemical Society ,
1986
15.
Matsubara S., Yoshioka M., Utimoto K.
Chemistry Letters ,
1994
16.
Matsunaga H., Sakamaki T., Nagaoka H., Yamada Y.
Tetrahedron Letters ,
1983
17.
Suminov S.I., Kost A.N.
Russian Chemical Reviews ,
1969
18.
Baldwin S.W., Aubé J.
Tetrahedron Letters ,
1987
19.
Matsumoto K., Sera A., Uchida T.
Synthesis ,
1985
20.
Es-Sayed M., Gratkowski C., Krass N., Meyers A.I., de Meijere A.
Tetrahedron Letters ,
1993
21.
Molander G.A.
Chemical Reviews ,
1992
22.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR ,
1958
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR ,
1951
24.
Rao K.R., Nageswar Y.V., Kumar H.M.
Tetrahedron Letters ,
1991
25.
Pyne S.G., Griffith R., Edwards M.
Tetrahedron Letters ,
1988
26.
Hawkins J.M., Fu G.C.
Journal of Organic Chemistry ,
1986
27.
Cox P.J., Simpkins N.S.
Tetrahedron Asymmetry ,
1991
28.
Asao N., Uyehara T., Yamamoto Y.
Tetrahedron ,
1988
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
30.
Rathke M.W., Sullivan D.
Tetrahedron Letters ,
1972
31.
Little R.D., Dawson J.R.
Tetrahedron Letters ,
1980
32.
Uyehara T., Shida N., Yamamoto Y.
Journal of Organic Chemistry ,
1992
33.
Bunnage M.E., Davies S.G., Goodwin C.J., Ichihara O.
Tetrahedron ,
1994
34.
Yamamoto Y., Asao N., Uyehara T.
Journal of the American Chemical Society ,
1992
35.
Davies S.G., Walters I.A.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
36.
Davies S.G., Fenwick D.R.
Journal of the Chemical Society Chemical Communications ,
1995
37.
Davies S.G., Ichihara O., Walters I.A.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
38.
Davies S.G., Ichihara O., Walters I.A.
Synlett ,
1994
39.
Davies S.G., Garrido N.M., Ichihara O., Walters L.A.
Journal of the Chemical Society Chemical Communications ,
1993
40.
Bunnage M.E., Burke A.J., Davies S.G., Goodwin C.J.
Tetrahedron Asymmetry ,
1995
41.
Davies S.G., Ichihara O., Lenoir I., Walters I.A.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
42.
Asao N., Tsukada N., Yamamoto Y.
Journal of the Chemical Society Chemical Communications ,
1993
43.
Davies S.G., Ichihara O., Walters L.A.
Synlett ,
1993
44.
Hawkins J.M., Lewis T.A.
Journal of Organic Chemistry ,
1992
45.
Hawkins J.M., Lewis T.A.
Journal of Organic Chemistry ,
1994
46.
Asao N., Shimada T., Tsukada N., Yamamoto Y.
Tetrahedron Letters ,
1994
47.
Rico J.G., Lindmark R.J., Rogers T.E., Bovy P.R.
Journal of Organic Chemistry ,
1993
48.
Costello J.F., Davies S.G., Ichihara O.
Tetrahedron Asymmetry ,
1994
49.
Davies S.G., Hedgecock C.J., McKenna J.M.
Tetrahedron Asymmetry ,
1995
50.
Suzuki I., Kin H., Yamamoto Y.
Journal of the American Chemical Society ,
1993
51.
52.
Uyehara T., Asao N., Yamamoto Y.
Journal of the Chemical Society Chemical Communications ,
1987
53.
Asao N., Uyehara T., Yamamoto Y.
Tetrahedron ,
1990
54.
Bunnage M.E., Chernega A.N., Davies S.G., Goodwin C.J.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
55.
Bunnage M.E., Davies S.G., Goodwin C.J.
Journal of the Chemical Society Perkin Transactions 1 ,
1993
56.
Bunnage M.E., Davies S.G., Goodwin C.J.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
57.
Bannage M.E., Burke A.J., Davies S.G., Goodwin C.J.
Tetrahedron Asymmetry ,
1994
58.
Bunnage M.E., Davies S.G., Goodwin C.J.
Synlett ,
1993
59.
Hosomi A., Yanagi T., Hojo M.
Tetrahedron Letters ,
1991
60.
Shida N., Uyehara T., Yamamoto Y.
Journal of Organic Chemistry ,
1992
61.
Shida N., Kabuto C., Niwa T., Ebata T., Yamamoto Y.
Journal of Organic Chemistry ,
1994
62.
Bunnage M.E., Davies S.G., Goodwin C.J., Walters I.A.
Tetrahedron Asymmetry ,
1994
63.
Amoroso R., Cardillo G., Sabatino P., Tomasini C., Trere A.
Journal of Organic Chemistry ,
1993
64.
Cardillo G., De Simone A., Gentilucci L., Sabatino P., Tomasini C.
Tetrahedron Letters ,
1994
65.
Uyehara T., Asao N., Yamamoto Y.
Journal of the Chemical Society Chemical Communications ,
1989
66.
Hirama M., Shigemoto T., Yamazaki Y., Ito S.
Journal of the American Chemical Society ,
1985
67.
Hirama M., Shigemoto T., Ito S.
Journal of Organic Chemistry ,
1987
68.
Shimano M., Meyers A.I.
Journal of Organic Chemistry ,
1995
69.
Enders D., Bettray W., Raabe G., Runsink J.
Synthesis ,
1994
70.
Rudolf K., Hawkins J.M., Loncharich R.J., Houk K.N.
Journal of Organic Chemistry ,
1988