S. R. Woodcock, B. P. Branchaud / Tetrahedron Letters 46 (2005) 7213–7215
7215
2694; Friestad, G. K.; Branchaud, B. P. Tetrahedron Lett.
1995, 36, 7047–7050.
9. Beautement, K.; Clough, J. M. Tetrahedron Lett. 1984, 25,
3025–3028.
3. Beckwith, A. L. J.; Gara, W. B. J. Chem. Soc., Perkin
Trans. 2 1975, 795–802.
10. Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16,
2647–2650.
4. Iyer, S.; Raimesh, C.; Ramani, A. Tetrahedron Lett. 1997,
38, 8533–8536.
11. Jeffery, T. Tetrahedron 1996, 52, 10113–10130.
12. Deziel, R. Tetrahedron Lett. 1987, 28, 4371–4372.
13. Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem.
Soc. 1995, 117, 7834–7835.
14. Amatore, C.; Azzabi, M.; Jutand, A. J. Am. Chem. Soc
1991, 113, 8375–8384.
5. Negishi, E.-i.; Nguyen, T.; OÕConnor, B.; Evans, J. M.;
Silviera, A., Jr. Heterocycles 1989, 28, 55–58.
6. Spectroscopic data for 7: 1H NMR (300 MHz, CDCl3):
7.94 (d, 1H), 7.75 (d, 1H), 7.36 (t, 1H), 7.10 (t, 1H), 5.98
(m, 1H), 5.86 (m, 1H), 5.50 (m, 1H), 2.2–1.6 (m, 6H). 13C
NMR (75 MHz, CDCl3): 166.4, 141.2, 135.7, 133.3, 132.5,
130.9, 127.9, 125.3, 94.0, 69.7, 28.3, 25.0, 18.9. IR (KBr,
cmÀ1) 2937, 1716, 1429, 1248.
15. Brown, J. M.; Perez-Torrente, J. J.; Alcock, N. W.; Clase,
H. J. Organometallics 1995, 14, 207–213.
16. Pampin, C.; Estevez, J. C.; Castedo, L.; Estevez, R. J.
Tetrahedron Lett. 2002, 43, 4551–4553.
1
7. Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck,
R. F. J. Org. Chem. 1983, 48, 3894–3900.
17. Spectroscopic data for 12: H NMR (300 MHz, CDCl3):
7.98 (dd, 2H), 7.84 (d, 1H), 7.72 (d, 1H), 7.54 (m, 2H), 7.5–
7.2 (m, 3H), 7.15 (t, 1H), 7.02 (d, 1H), 6.05 (m, 1H), 5.46
(d, 1H), 5.32 (m, 1H), 4.84 (d, 2H). IR (KBr, cmÀ1) 2942,
1727, 1248, 1131. APCI MS m/z (M+1) calcd 265.1, obsd
265.0, 265.2. Spectroscopic data for 13: 1H NMR
(300 MHz, CDCl3): 7.98 (d, 1H), 7.92 (d, 1H), 7.71 (d,
1H), 7.6–7.5 (m, 3H), 7.4–7.2 (m, 4H), 6.99 (d, 1H), 6.03
(d, 1H), 5.80 (m, 1H), 5.53 (d, 1H) 2.1–1.6 (m, 6H). IR
(KBr, cmÀ1) 2940, 1708, 1246, 1131. APCI MS m/z (M+1)
calcd 305.2, obsd 305.0.
1
8. Spectroscopic data for 6a: H NMR (300 MHz, CDCl3):
7.3–7.2 (m, 3H), 7.01 (d, 1H), 5.78 (m, 1H), 5.66 (d, 1H),
4.87 (s, 2H), 4.08 (br s, 1H), 3.33 (br s, 1H) 2.4–1.8 (m,
4H). 13C NMR (75 MHz, CDCl3): 136.8, 134.5, 129.0,
128.9, 127.0, 126.5, 126.2, 124.3, 71.4, 68.0, 37.7, 27.2,
20.0. IR (KBr, cmÀ1) 2922, 2841, 1490, 1448, 1099. APCI
MS m/z (MÀ1) calcd 185.1, obsd 185.0. Spectroscopic
1
data for 8a: H NMR (300 MHz, CDCl3): 8.10 (d, 1H),
7.55 (t, 1H), 7.40 (t, 1H), 7.29 (d, 1H), 5.79 (m, 1H), 5.68
(d, 1H), 4.82 (s, 1H), 2.98 (m, 1H) 2.55 (s, 2H), 2.4–1.8
(m, 2H). 13C NMR (75 MHz, CDCl3): 166.2, 133.9, 130.9,
127.9, 126.6, 125.9, 123.1, 75.3, 35.6, 30.2, 28.8. IR (KBr,
cmÀ1) 2917, 1724, 1270, 1115. APCI MS m/z (M+1) calcd
201.1, obsd 201.0.
18. Eliel, E. L.; Wilen, S. H. In Stereochemistry of Organic
Compounds, 2nd ed.; Wiley-Interscience: New York, 1994,
pp 618–619, and references cited therein.
19. Imase, T.; Kawauchi, S.; Watanabe, J. Macromol. Theory
Simul. 2001, 10, 434–440.