386
N. Azizi, M. R. Saidi / Tetrahedron 60 (2004) 383–387
Scheme 2.
2. Experimental
2.2.9. Methyl 3-phenyl-3-(N-buthylamino)-propionate.
See Table 1, entry 10.4f
2.1. General
2.2.10. Methyl 2-methyl-3-pyrrolidinylpropionate. See
Table 1, entry 11.1b
NMR spectra were recorded on a Bruker ACF 500. IR
spectra were measured using a Perkin–Elmer 1600 FTIR
spectrometer. Column chromatography was performed on
silica gel, Merck grade 60. CH2Cl2 was distilled before use.
All reactions were performed under argon. Anhydrous
LiClO4 and other chemicals were purchased from Fluka or
Merck.
2.2.11. Methyl 2-methyl-3-(N,N-diethylamino)propio-
nate. See Table 1, entry 13.1b
2.2.12. 3-Pyrrolidinyl-propionitrile. See Table 2, entry
1.4b
Caution. Although we did not have any accident while using
or drying LiClO4, it is advisable to dry lithium perchlorate
in hood using suitable lab-shield.
2.2.13. 3-(N,N-Diethylamino)-propionitrile. See Table 1,
entry 3.1b
2.2.14. 3-(N-Buthylamino)-propionitril. See Table 1,
entry 5.1a
2.2. General procedure for the preparation of the
Michael reaction of amines with a,b-unsaturated olefins
2.2.15. 3-Pyrrolidinylpropionamide. See Table 2, entry
8.1c
To a mixture of LiClO4 (2 mmol) and methyl acrylate
(2 mmol) was added pyrrolidine (3 mmol) and was stirred at
room temperature under an argon atmosphere for 1 h. After
completion of the reaction, CH2Cl2 (10 mL) was added, and
LiClO4 was removed by filtration. The solvent was
evaporated and the product was isolated in almost pure
from. Further purification was carried out by short column
chromatography on silica gel eluting with ethyl acetate/
petroleum ether. All compounds were characterized by
retention times in GC and on the basis of their
spectroscopic data (IR, NMR, MS) and by comparison
with those reported in the literature.
2.2.16. 3-(N,N-Diethylamino)-propionamide. See Table 2,
entry 10.1c
2.2.17. 4-(N-Phenylamino)-2-butanone. See Table 2, entry
13.1b
References and notes
1. (a) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991. and
reference cited therein. (b) Cole, D. E. Tetrahedron 1994, 50,
9517, and reference cited therein. (c) In Enantioselective
Synthesis of B-amino Acids; Juaristi, E., Ed.; Wiley-VCH: New
York, 1997; Chapters 11–13. (d) Hart, D. J.; Ha, D.-C. Chem.
Rev. 1989, 89, 1447. (e) Van der Steen, F. H.; Van Koten, G.
Tetrahedron 1991, 47, 7503. (f) Cardillo, G.; Tomasini, C.
Chem. Soc. Rev. 1996, 117. (g) Hattori, K.; Miyata, M.;
Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 1151. (h) Bongini,
A.; Cardillo, G.; Orena, M.; Porzi, G.; Sandri, S. Tetrahedron
1987, 43, 4377. (i) Hecht, S. M. Acc. Chem. Res. 1986, 19, 383.
(j) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (k)
Juaristi, E.; Quintana, D.; Escalante, J. Aldrichim. Acta 1994,
27, 3.
2.2.1. Methyl 3-pyrrolidinyl-propionate. See Table 1,
entry 1.4f
2.2.2. Methyl 3-piperidinyl-propionate. See Table 1, entry
2.4f
2.2.3. Methyl 3-(N,N-diethylamino)-propionate. See
Table 1, entry 3.4f
2.2.4. Methyl 3-(N-benzylamino)-propionate. See Table
1, entry 4.4f
2.2.5. Methyl 3-(N-buthylamino)-propionate. See Table
1, entry 5.1b
2. (a) Vicario, J. L.; Badia, D.; Carrillo, L. Org. Lett. 2001, 3, 773.
(b) Gellman, S. Acc. Chem. Res. 1998, 31, 173.
2.2.6. Methyl 3-(N-phenylamino)-propionate. See Table
1, entry 6.1b
3. (a) Jenner, G. Tetrahedron Lett. 1995, 36, 233. (b) D’Angelo, J.;
Maddaluno, J. J. Am. Chem. Soc. 1986, 108, 8112.
4. (a) Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 720. (b)
Bartoli, G.; Bosco, M.; Marcantoni, E.; Petrini, M.; Sambri, L.;
Torregiani, E. J. Org. Chem. 2001, 66, 9052. (c) Shaikh, N. S.;
Deshpande, V. H.; Bedekar, A. V. Tetrahedron 2001, 9045. (d)
Loh, T. P.; Wei, L.-L. Synlett 1998, 975. (e) Ben Ayed, T.;
Amiri, H.; EL Gaied, M. M.; Villieras, J. Tetrahedron 1995, 35,
2.2.7. Methyl 3-(1-phenylethylamino)-propionate. See
Table 1, entry 7.1a
2.2.8. Methyl 3-phenyl-3-pyrrolidinylpropionate. See
Table 1, entry 8.4f