5424
T. Hirashita et al. / Tetrahedron Letters 48 (2007) 5421–5424
3.4. GaCl -mediated reaction of trimethyl(propargyl)-
silane with imine 1b
2. Lewis acids catalyzed reaction of electron-rich olefines:
Enol ether: Crousse, B.; B e´ gu e´ , J.-P.; Bonnet-Delpon, D.
Tetrahedron Lett. 1998, 39, 5765–5768; Kobayashi, S.;
Ishitani, H.; Nagayama, S. Synthesis 1995, 1195–1202; 1,3-
Diene: Alves, M. J.; Azoia, N. G.; Fortes, A. G.
Tetrahedron 2007, 63, 727–734; Styrene: Fadel, F.; Titou-
ani, S. L.; Soufiaoui, M.; Ajamaya, H.; Mazzah, A.
Tetrahedron Lett. 2004, 45, 5905–5908.
3
(
Table 3, entry 4) To a solution of imine 1b (113 mg,
.50 mmol) and chloranil (124 mg, 0.50 mmol) in
CH Cl (2 mL), GaCl3 (1.0 M in CH Cl , 0.25 mL,
0
2
2
2
2
0
.25 mmol) was added at 0 ꢁC and the mixture was
stirred for 5 min. Trimethyl(propargyl)silane (120 lL,
.75 mmol) was added and the reaction mixture was
´
3
. Kuznetsov, V. V.; Aliev, A. E.; Prostakov, N. S. Chem.
0
Heterocycl. Compd. 1994, 30, 64–68.
stirred at room temperature for 1 h. After quenching
by water (2 mL), the products were extracted with
diethyl ether. The extracts were washed with brine and
dried on Na SO . After the solvent was removed under
reduced pressure, the residue was separated by chroma-
tography on silica gel (hexane–EtOAc = 30:1 then
EtOAc) to give 5 (85 mg, 64%) and recovered 1b
4. Akiyama, T.; Suzuki, M.; Kagoshima, H. Heterocycles
2000, 52, 529–532.
5
6
7
. (a) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17,
1
2
295–1298; (b) Hosomi, A. Acc. Chem. Res. 1988, 21, 200–
06.
2
4
. Yamaguchi, M. In Main Group Metals in Organic
Synthesis; Yamamoto, H., Oshima, K., Eds.; Wiley-
VCH: Weinheim, 2005; Vol. 1, pp 307–322.
. (a) Calas, R.; Dunogues, J.; Deleris, G.; Pisciotti, F. J.
Organomet. Chem. 1974, 69, C15–C17; (b) Deleris, G.;
Dunogues, J.; Calas, R. J. Organomet. Chem. 1975, 93,
(
12 mg, 11%).
1
5
3
.5. 4-Methyl-2-(4-nitrophenyl)quinoline (5)
4
3–50.
1
8
. Yamaguchi, M.; Sotokawa, T.; Hirama, M. J. Chem. Soc.,
Chem. Commun. 1997, 743–744.
H NMR (200 MHz, CDCl , d ppm): 2.82 (s, 3H), 7.61
3
(
t, 1H, J = 7.0 Hz), 7.73–7.82 (m, 2H), 8.04 (d, 1H,
9
. Onishi, Y.; Ito, T.; Yasuda, M.; Baba, A. Tetrahedron
J = 7.0 Hz), 8.19 (d, 1H, J = 8.0 Hz), 8.30–8.41 (m, 4H).
2
002, 58, 8227–8235.
1
0. (a) Pornet, J. Tetrahedron Lett. 1981, 22, 453–454; (b)
Coppi, L.; Ricci, A.; Taddei, M. Tetrahedron Lett. 1987,
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Mann, A. Tetrahedron Lett. 2002, 43, 1453–1456.
1. Niimi, L.; Shiino, K.; Hiraoka, S.; Yokozawa, T. Tetra-
hedron Lett. 2001, 42, 1721–1724.
2. Saito, T.; Nishimoto, Y.; Yasuda, M.; Baba, A. J. Org.
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Acknowledgment
1
1
1
This work was partially supported by a Grant-in-Aid for
Scientific Research (No. 14340195) from the Ministry of
Education, Science, Sport and Culture, Japan.
References and notes
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