H. Murata et al. / Tetrahedron Letters 49 (2008) 4788–4791
4791
11. (a) Itoh, A.; Kodama, T.; Maeda, S.; Masaki, Y. Tetrahedron Lett. 1998, 39, 9461–
9464; Itoh, A.; Kodama, T.; Masaki, Y. Chem. Pharm. Bull. 2007, 55, 861–864;
(c)(b) Yamamoto, T.; Tanaka, T.; Funabiki, T.; Yoshida, S. J. Phys. Chem. B 1998,
102, 5830–5839.
tuted propionic acid esters were directly obtained through the
reaction.
12. Abe, T.; Tachibana, Y.; Uematsu, T.; Iwamoto, M. J. Chem. Soc., Chem. Commun.
1995, 1617–1618.
13. Iwamoto, M.; Tanaka, Y. Catal. Surv. Jpn. 2001, 5, 25–36.
References and notes
14. Typical procedure for b-ketoester preparation:
a solution of aldehyde 1
1. Several preparation methods of b-keto esters such as Claisen condensations
were described below: (a) Benetti, S.; Romagnoli, R.; Risi, C. D.; Spalluto, G.;
Zanirato, V. Chem. Rev. 1995, 95, 1065–1114; (b) Smith, M. B.; March, J.
Advanced Organic Chemistry, 5th ed.; Benjamin: New York, 2001; pp 569–573;
(c) Iida, A.; Takai, K.; Okabayashi, T.; Misaki, T.; Tanabe, Y. Chem. Commun.
2005, 3171–3173; (d) Sato, T.; Itoh, T.; Fujiwara, T. Chem. Lett. 1982, 1559–
1560.
(0.50 mmol) with tetradecane (0.10 mmol, internal standard) in 2.0 mL
distilled CH2Cl2 was added to the evacuated M41s. Then, 0.75 mmol of
diazoester
2 with 0.5 mL of CH2Cl2 were dropwised into the suspension
(30 min). After 14 hour, the reaction media was diluted by CH2Cl2 and the
catalyst was removed by the filtration. Yield was determined by preparative
TLC or GC.
15. 3b was 65% yield when CH2Cl2 was used as a solvent.
16. Ethyl diazoacetate 2a was added at a stroke.
2. (a) Schlotterbeck, F. Chem. Ber. 1909, 42, 2565–2573; (b) Curtius, T.; Buchner, E.
Chem. Ber. 1885, 18, 2371–2377.
17. Physical data of representative compounds: 3i: 1H NMR (400 MHz; CDCl3/TMS) d
(ppm) 0.83 (t, 3H, J = 7.0), 1.14–1.21 (m, 6H), 1.45–1.57 (m, 2H), 2.08 (t, 0.6H,
J = 8.0), 2.44 (t, 1.4H, J = 7.2), 4.76 (s, 0.7H), 5.19 (s, 2H), 7.15–7.19 (m, 1H),
7.27–7.38 (m, 9H). 13C NMR (100 MHz, CDCl3/TMS): d (ppm) 13.98, 22.42,
23.56, 26.63, 28.51, 28.83, 31.39, 31.43, 32.80, 41.64, 64.92, 65.76, 67.26,
127.02, 127.14, 127.80, 128.05, 128.26, 128.35, 128.38, 128.56, 128.83, 129.47,
131.33, 132.50, 135.40, 168.45, 203.65. Anal. for C22H26O3 (338.19). Calcd: C,
78.07; H, 7.74; O, 14.18. Obsd: C, 77.67; H, 8.00; O, 14.89. Compound 3j: 1H
NMR (400 MHz, CDCl3/TMS): d (ppm) 2.27 (s, 3H), 5.16 (s, 2H), 5.64 (s, 1H),
7.10–7.40 (m, 12H), 7.81 (d, 2H). 13C NMR (100 MHz, CDCl3/TMS): d (ppm)
21.5, 60.41, 67.23, 126.32, 126.75, 127.27, 127.43, 127.90, 128.10, 128.24,
128.75, 129.13, 133.06, 135.56, 144.41, 168.77, 192.69. Anal. for C23H20O3
(338.19). Calcd: C, 80.21; H, 5.85; O, 13.94. Obsd: C, 79.30; H, 6.02; O, 16.23.
The amounts of carbon and hydrogen were analyzed in a usual manner with a
CHNS-932 system of LECO Corporation. The oxygen content was separately
determined with a CHNS-932 system using a VFT-900 furnace operated at
1573 K.
3. Holmquist, C. R.; Roskamp, E. J. J. Org. Chem. 1989, 54, 3258–3260.
4. Yadav, J. S.; Subba Reddy, B. V.; Eeshwaraiah, B.; Reddy, P. N. Tetrahedron 2005,
61, 875–878.
5. Dhavale, D. D.; Patil, P. N.; Mali, R. S. J. Chem. Res. (S) 1994, 152–153.
6. Balaji, B. S.; Chanda, B. M. Tetrahedron 1998, 54, 13237–13252.
7. Phukan, P.; Mohan, J. M.; Sudalai, A. J. Chem. Soc., Perkin Trans. 1 1999, 3685–
3689.
8. (a) Mahmood, S. J.; Hossain, M. M. J. Org. Chem. 1998, 63, 3333–3336; (b)
Dudley, M. E.; Morshed, M. M.; Brennan, C. L.; Islam, M. S.; Ahmad, M. S.; Atuu,
M.; Branstetter, B.; Hossain, M. M. J. Org. Chem. 2004, 69, 7599–7608.
9. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Eur. J. Org. Chem. 2002,
1562–1565.
10. (a) Tanaka, Y.; Sawamura, N.; Iwamoto, M. Tetrahedron Lett. 1998, 39, 9457–
9460; (b) Iwamoto, M.; Yasuhiro, T.; Sawammura, N.; Namba, S. J. Am. Chem.
Soc. 2003, 125, 13032–13033; (c) Ishitani, H.; Iwamoto, M. Tetrahedron Lett.
2003, 44, 299–301.