Shaterian et al.
383
2. Y. Nishiyama, C. Katahira, and N. Sonoda. Tetrahedron Lett.
45, 8539 (2004).
3. D.E. Portlock, D. Naskar, L. West, R. Ostaszewski, and J.J.
(43), 77.2 (6), 65.2 (14), 43.2 (26). C18H18N2O4 requires (%):
C 66.25, H 5.56, N 8.58; found: C 66.23, H 5.56, N 8.51.
Chen. Tetrahedron Lett. 44, 5121 (2003).
N-[1-(4-Methylphenyl)-3-oxo-3-(4-methylphenyl)propyl]
acetamide
4. A. Fayol and J. Zhu. Org. Lett. 7, 239 (2005).
5. I. Ugi, A. Dömling, and B. Werner. J. Heterocycl. Chem. 37,
647 (2000).
Table 2, entry 22. IR (KBr, cm–1): 3258, 3069, 1607,
1638, 1605, 1541, 1410, 1326, 1266, 1183, 998, 810, 722.
1H NMR (300 MHz, DMSO-d6, ppm) δ: 1.77 (s, 3H), 2.24
(s, 3H), 2.36 (s, 3H), 3.31 (dd, J = 6.1 and 15.9 Hz, 1H),
3.46 (dd, J = 8.0 and 16.7 Hz, 1H), 5.31 (dd, J = 7.7 and
14.2 Hz, 1H), 7.10 (d, J = 7.9 Hz, 2H), 7.21 (d, J = 8.0 Hz,
2H), 7.31 (d, J = 8.0 Hz, 2H), 7.83 (d, J = 8.1 Hz, 2H), 8.25
(d, J = 8.0 Hz, 1H). 13C NMR (75 MHz, DMSO-d6, ppm) δ:
20.6, 21.1, 22.6, 44.5, 48.8, 126.5, 128.1, 128.7, 129.2,
134.1, 135.8, 140.0, 143.5, 168.2, 196.7. MS m/z (%): 295.2
(M+, 12), 252.2 (100), 253.2 (21), 221.2 (13), 162.2 (10),
134.2 (49), 120.2 (70), 119.2 (91), 91.2 (44), 65.2 (14), 43.2
(14). C19H21NO2 requires (%): C 77.26, H 7.17, N 4.74;
found: C 77.20, H 7.13, N 4.70.
6. A. Basso, L. Banfi, R. Riva, and G. Guanti. Tetrahedron Lett.
45, 587 (2004).
7. A. Basso, L. Banfi, R. Riva, and G. Guanti. J. Org. Chem. 70,
575 (2005).
8. (a) T. Nishio and M. Ori. Helv. Chim. Acta, 84, 2347 (2001);
(b) M. Ori and T. Nishio. Heterocycles, 52, 111 (2000).
9. (a) J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero, and
B. Olano. J. Org. Chem. 58, 5972 (1993); (b) A.G. Godfrey,
D.A. Brooks, L.A. Hay, M. Peters, J.R. McCarthy, and
D. Mitchell. J. Org. Chem. 68, 2623 (2003); (c) J.R. Casimir,
C. Turetta, L. Ettouati, and J. Paris. Tetrahedron Lett. 36, 4797
(1995); (d) K. Kobinata, M. Uramoto, M. Nishii, H. Kusakabi,
J. Nakamura, and K. Isono. Agric. Biol. Chem. 44, 1709 (1980).
10. M. Mukhopadhyay, B. Bhatia, and J. Iqbal. Tetrahedron Lett.
38, 1083 (1997).
(R)-Methyl 2-((S)-acetamido(phenyl)methyl)-3-
oxobutanoate
11. B. Bhatia, M.M. Reddy, and J. Iqbal. J. Chem. Soc. Chem.
Commun. 713 (1994).
12. D. Bahulayan, S.K. Das, and J. Iqbal. J. Org. Chem. 68, 5735
(2003).
Table 3, entry 1 (mixture of diastereomers), data for the
1
major isomer. H NMR (500 MHz, CDCl3, ppm) δ: 1.97 (s,
3H), 2.11 (s, 3H), 3.71 (s, 3H), 4.07 (d, J = 5.5 Hz, 1H),
5.72 (dd, J = 5.5 and 9.0 Hz, 1H), 6.91 (d, J = 8.1 Hz, 1H),
7.22–7.30 (m, 5H).
13. M.M. Khodaei, A.R. Khosropour, and P. Fattahpour. Tetrahe-
dron Lett. 46, 2105 (2005).
14. R. Ghosh, S. Maity, and A. Chakraborty. Synlett. 115 (2005).
15. R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty, and A.K.
Mukherjee. Tetrahedron, 62, 4059 (2006).
(R)-Methyl 2-((S)-acetamido(4-chlorophenyl)methyl)-3-
oxobutanoate
16. E. Rafiee, F. Tork, and M. Joshaghani. Bioorg. Med. Chem.
Table 3, entry 2 (mixture of diastereomers), data for the
Lett. 16, 1221 (2006).
1
major isomer. H NMR (500 MHz, CDCl3, ppm) δ: 1.98 (s,
17. T. Yakaiah, V.G. Reddy, B.P.V. Lingaiah, B. Narsaiah, and P.
Shanthan Rao. Synth. Commun. 35, 1307 (2005).
18. G. Pandey, R.P. Singh, A. Garg, and V.K. Singh. Tetrahedron
Lett. 46, 2137 (2005).
3H), 2.13 (s, 3H), 3.73 (s, 3H), 4.07 (d, J = 5.5 Hz, 1H),
5.69 (dd, J = 5.5 and 9.0 Hz, 1H), 6.93 (d, J = 8.3 Hz, 1H),
7.20 (d, J = 8.8 Hz, 2H), 7.26(d, J = 7.9 Hz, 2H).
19. E. Rafiee, F. Shahbazi, M. Joshaghani, and F. Tork. J. Mol.
(R)-Ethyl 2-((S)-acetamido(phenyl)methyl)-3-
oxobutanoate
Catal. A: Chem. 242, 129 (2005).
20. L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri, and
V. Kumari. J. Mol. Catal. A: Chem. 264, 22 (2007).
21. A.T. Khan, L.H. Choudhury, T. Parvin, and M. Asif Ali. Tetra-
hedron Lett. 47, 8137 (2006).
22. M.T. Maghsoodlou, A. Hassankhani, H.R. Shaterian, S.M.
Habibi-Khorasania, and E. Mosaddegh. Tetrahedron Lett. 48,
1729 (2007).
Table 3, entry 4 (mixture of diastereomers), data for the
1
major isomer. H NMR (500 MHz, CDCl3, ppm) δ: 1.20 (t,
J = 7.1 Hz, 3H), 1.99 (s, 3H), 2.16 (s, 3H), 4.01 (d, J =
5.9 Hz, 1H), 4.15 (q, J = 7.0 Hz, 2H), 5.76 (dd, J = 6.2 and
8.9 Hz, 1H), 6.99 (d, J = 8.8 Hz, 1H), 7.24–7.33 (m, 5H).
23. B. Das, K.R. Reddy, R. Ramu, P. Thirupathi, and B.
Ravikanth. Synlett. 1756 (2006).
24. B. Das, M. Krishnaiah, K. Laxminarayana, and K.R. Reddy. J.
Mol. Catal. A: Chem. 270, 284 (2007).
25. A.T. Khan, T. Parvin, and L.H. Choudhury. Tetrahedron, 63,
5593 (2007).
N-((1S,2R)-2-Methyl-3-oxo-1,3-diphenylpropyl)acetamide
Table 3, entry 6 (mixture of diastereomers), data for the ma-
1
jor isomer. H NMR (500 MHz, CDCl3, ppm) δ: 1.32 (d, J =
7.2 Hz, 3H), 2.04 (s, 3H), 4.03–4.13 (m, 1H), 5.35 (dd, J = 4.5
and 8.9 Hz, 1H), 6.99–7.27 (m, 9H), 7.79 (d, J = 7.4 Hz, 2H).
26. B. Das, K.R. Reddy, Y. Srinivas, and R.A. Kumar. Can. J.
Acknowledgments
Chem. 85, 479 (2007).
27. F. Shirini, M.A. Zolfigol, and B. Mallakpour. Russ. J. Org.
Chem. 41, 625 (2005).
28. F. Shirini, M.A. Zolfigol, B. Mallakpour, S.E. Mallakpour, A.R.
Hajipour, and I.M. Baltork. Tetrahedron Lett. 43, 1555 (2002).
29. F. Shirini, M.A. Zolfigol, B. Mallakpour, I.M. Baltork, and
A.R. Hajipour. J. Chem. Res. 28 (2003).
We are thankful to the Sistan and Baluchestan University
Research Council for partial support of this work.
References
1. (a) C. Hulme and V. Gore. Curr. Med. Chem. 10, 51 (2003);
(b) C. Hulme and T. Nixey. Curr. Opin. Drug Discovery Today,
6, 921 (2003).
© 2008 NRC Canada