Y. Wu et al. / Tetrahedron Letters 50 (2009) 3683–3685
3685
4. Asao,N.;Yudha,S.S.;Nogami,T.;Yamamoto,Y.Angew.Chem.,Int.Ed.2005,44,5526.
5. (a) Yanada, R.; Obika, S.; Kono, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2006, 45,
3822; (b) Obika, S.; Kono, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. J. Org. Chem.
2007, 72, 4462; (c) Ding, Q.; Yu, X.; Wu, J. Tetrahedron Lett. 2008, 49, 2752.
6. (a) Ye, Y.; Ding, Q.; Wu, J. Tetrahedron 2008, 64, 1378; (b) Ding, Q.; Wu, J. Org.
Lett. 2007, 9, 4959.
7. (a) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450; (b) Ma, D.; Zhang, Y.; Yao, J.;
Wu, S.; Tao, T. J. Am. Chem. Soc. 1998, 120, 12459; (c) Ma, D.; Xia, C. Org. Lett.
2001, 3, 2583; (d) Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
8. (a) Xie, X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693; (b) Xie, X.; Chen, Y.; Ma, D. J.
Am. Chem. Soc. 2006, 128, 16050.
9. Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem. 2007, 72, 5337.
10. Zou, B.; Yuan, Q.; Ma, D. Angew. Chem., Int. Ed. 2007, 46, 2598.
11. Zou, B.; Yuan, Q.; Ma, D. Org. Lett. 2007, 9, 4291.
12. (a) Liu, F.; Ma, D. J. Org. Chem. 2007, 72, 4884; (b) Chen, Y.; Xie, X.; Ma, D. J. Org.
Chem. 2007, 72, 9329; (c) Chen, Y.; Wang, Y.; Sun, Z.; Ma, D. Org. Lett. 2008, 10,
625.
13. Wang, B.; Lu, B.; Jiang, Y.; Zhang, Y.; Ma, D. Org. Lett. 2008, 10, 2761.
14. For selected recent examples on the assembly of heterocycles via Ullmann-
type coupling reactions, see: (a) Guo, L.; Li, B.; Huang, W.; Pei, G.; Ma, D. Synlett
2008, 1833; (b) Minatti, A.; Buchwald, S. L. Org. Lett. 2008, 10, 2721; (c)
Hasegawa, K.; Kimura, N.; Arai, S.; Nishida, A. J. Org. Chem. 2008, 73, 6363; (d)
Viirre, R. D.; Evindar, G.; Batey, R. A. J. Org. Chem. 2008, 73, 3452; (e) Jones, C. P.;
Anderson, K. W.; Buchwald, S. L. J. Org. Chem. 2007, 72, 7968; (f) Yang, D.; Fu,
H.; Hu, L.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 7841; (g) Yuan, Q.; Ma, D. J.
Org. Chem. 2008, 73, 5159; (h) Yuan, X.; Xu, X.; Zhou, X.; Yuan, J.; Mai, L.; Li, Y. J.
Org. Chem. 2007, 72, 1510; (i) Pan, Y.; Lu, H.; Fang, Y.; Fang, X.; Chen, L.; Qian, J.;
Wang, J.; Li, C. Synthesis 2007, 8, 1242; (j) Bao, W.; Liu, Y.; Lv, X.; Qian, W. Org.
Lett. 2008, 10, 3899; (k) Chen, L.; Shi, M.; Li, C. Org. Lett. 2008, 10, 5285.
15. (a) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268; (b) Wei, C.; Li, C.-J. J. Am. Chem.
Soc. 2002, 124, 5638; (c) Shi, L.; Tu, Y.; Wang, M.; Zhang, F.; Fan, C. Org. Lett.
2004, 6, 1001; (d) Yoo, W.-J.; Li, C.-J. Adv. Synth. Catal. 2008, 350, 1503; (e)
Nguyen, R.-V.; Li, C.-J. Synlett 2008, 1897; (f) Zhang, J.; Wei, C.; Li, C.-J.
Tetrahedron Lett. 2002, 43, 5731; (g) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472.
16. Typical procedure for copper-catalyzed cascade process: An oven-dried Schlenk
tube was charged with CuI (0.05 mmol), potassium carbonate (1.5 mmol),
and 1-(2-bromophenyl)-propargylamine 4a (0.5 mmol). The tube was
evacuated and backfilled with argon, methyl acetoacetate 5a (1.0 mmol)
was added into the tube followed by i-PrOH–H2O (3:1, 2.4 mL). The reaction
mixture was stirred at 50 °C. After 12 h, the mixture was cooled, then
partitioned between ethyl acetate and brine. The organic layer was isolated,
and the water phase was extracted with ethyl acetate. The assembled
organic phase was dried over Na2SO4, and concentrated in vacuo. The
residue was purified by silica gel chromatography to give 7a. 1H NMR
(300 MHz, CDCl3) d 2.41 (s, 3H), 3.83 (s, 3H), 4.14 (dd, J = 5.7, 16.8 Hz, 1H),
4.23 (dd, J = 4.5, 16.8 Hz, 1H), 5.23–5.32 (m, 2H), 5.33 (s, 1H), 5.84–5.96 (m,
1H), 7.12–7.18 (m, 2H), 7.23–7.28 (m, 4H), 7.35–7.38 (m, 2H), 7.67 (d,
J = 8.1 Hz, 1H); 13C NMR (100 MHz, CDCl3)
d 17.96, 51.15, 52.47, 53.91,
85.26, 87.08, 102.87, 117.97, 122.87, 124.06, 124.88, 125.22, 127.08, 128.08,
128.43 (2*C), 128.62, 131.86, 132.10 (2*C), 133.72, 152.67, 169.29; ESI-MS m/
z 344.1 (M+H)+, 365.9 (M+Na)+; EI-HRMS cacld for C23H21NO2 (M)+ requires
343.1572, found 343.1578.