J. R. Falck et al. / Tetrahedron Letters 43 (2002) 8149–8151
8151
ature, filtered, diluted with an equal volume of Et2O,
washed with H2O (10 mL), brine (10 mL), dried and
concentrated in vacuo. Purification of the residue via
SiO2 chromatography provided the adducts in the indi-
cated yields (Table 1).
1.50–1.72 (m, 2H), 2.55–2.65 (m, 2H), 4.80–4.91 (bs, 2H),
6.91–7.02 (m, 2H), 7.07–7.18 (m, 2H); 13C NMR (100
MHz, CDCl3) l 17.1, 28.2, 34.4, 36.8, 115.3, 130.2, 134.8,
160.2. 6: 1H NMR l 1.73–2.01 (s, 12H), 2.55 (t, 4H,
J=7.6 Hz), 6.91–6.98 (m, 4H), 7.09–7.14 (m, 4H); 13C
NMR l 30.0, 30.3, 32.3, 36.2, 114.9, 129.5, 134.5, 160.2.
9 pinacol ester: 1H NMR l 1.24 (d, 12H, J=3.3 Hz),
1.25–1.48 (m, 2H), 1.60–1.83 (m, 4H), 2.58–2.65 (m, 2H),
3.16 (t, 1H, J=8.1 Hz), 3.32 (s, 3H), 7.14–7.27 (m, 5H);
13C NMR l 21.5, 23.6, 25.8, 32.9, 35.6, 55.1, 73.0, 88.8,
125.5, 127.7, 127.9, 135.5. 10 (mixture of erythro/threo-
stereoisomers: 1H NMR l 1.31–1.68 (m, 12H), 2.61 (t,
4H, J=7.6 Hz), 3.08–3.13 (m, 2H), 3.30 (s, 3H), 3.31 (s,
3H), 7.18–7.39 (m, 10H); 13C NMR l 23.5, 23.8, 24.4,
28.6, 30.4, 31.5, 32.9, 54.4, 55.0, 79.0, 82.2, 125.3, 127.9,
130.2, 135.2. 12: 1H NMR l 1.71 (apparent quintet,
J=7.3 Hz), 2.10 (apparent quintet, 4H, J=7.3 Hz), 2.62
(t, 4H, J=7.8 Hz), 5.54–5.64 (m, 2H), 5.98–6.08 (m, 2H),
7.18–7.22 (m, 6H), 7.25–7.30 (m, 4H); 13C NMR l 29.9,
Acknowledgements
Supported financially by the USPHS NIH (GM31278,
DK38226), the Robert A. Welch Foundation, and an
unrestricted grant from Taisho Pharmaceutical Co.,
Ltd.
References
1. Miyaura, N.; Suzuki, A. Main Group Met. Chem. 1987,
10, 295–300.
2. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire,
M. Chem. Rev. 2002, 102, 1359–1469.
3. Nonhebel, D. C. Chem. Soc., Spec. Publ. 1970, 24, 409–
437.
1
35.4, 36.2, 125.4, 127.6, 128.3, 128.5, 133.2, 138.3. 22: H
NMR l 0.85–0.92 (m, 6H), 1.21–1.45 (m, 12H), 2.05–2.20
(m, 4H), 3.40 (d, 4H, J=6.1 Hz), 5.52–5.56 (m, 4H),
7.18–7.32 (m, 8H); 13C NMR l 14.9, 22.7, 26.7, 30.2,
32.4, 34.1, 125.9, 126.6, 129.2, 129.5, 130.0, 134.6, 138.8,
4. Kabalka, G. W.; Wang, L. Tetrahedron Lett. 2002, 43,
3067–3068.
1
139.1. 23: H NMR (300 MHz): l 2.09 (s, 3H), 4.73 (d,
2H, J=6.3 Hz), 4.76–4.85 (bs, 2H), 6.05–6.15 (m, 1H),
7.10 (d, 1H, J=16.6 Hz), 7.25–7.31 (m, 1H), 7.37–7.44
(m, 4H), 7.69 (d, 1H, J=7.0 Hz); 13C NMR l 18.0, 70.6,
123.2, 125.6, 126.8, 127.3, 127.7, 128.4, 128.5, 136.6,
174.6. 24: 1H NMR l 2.01 (s, 6H), 4.54 (d, 2H, J=6.1
Hz), 6.13–6.20 (m, 2H), 6.28 (d, 2H, J=15.8 Hz), 7.14 (d,
2H, J=7.3 Hz), 7.29–7.38 (m, 4H), 7.62 (d, 2H, J=7.6
Hz); 13C NMR l 18.4, 71.7, 175.1, 125.8, 126.1, 126.6,
126.7, 127.2, 127.7, 132.6, 136.2. 27: 1H NMR l 2.84–
2.88 (m, 2H), 2.95–3.01 (m, 2H), 5.31 (dd, J=9.7, 1.2 Hz,
1H), 6.66 (dd, J=15.8, 1.5 Hz, 1H); 6.97–7.04 (m, 1H),
7.15–7.28 (m, 8H), 7.49–7.51 (m, 1H); 13C NMR l 35.8,
36.9, 114.8, 126.0, 126.1, 127.3, 127.7, 128.5, 129.7, 133.6,
136.6, 136.8, 141.3.
5. Lei, A.; Zhang, X. Tetrahedron Lett. 2002, 43, 2525–2528.
6. Smith, K. A.; Campi, E. M.; Jackson, W. R.; Marcuccio,
S.; Naeslund, C. G. M.; Deacon, G. B. Synlett 1997, 1,
131–132.
7. Wong, M. S.; Zhang, X. L. Tetrahedron Lett. 2001, 42,
4087–4089.
8. Snyder, H. R.; Kuck, J. A.; Johnson, J. R. J. Am. Chem.
Soc. 1938, 60, 105–111.
9. Johnson, J. R.; Van Campen, M. G., Jr.; Grummitt, O. J.
Am. Chem. Soc. 1938, 60, 111–115.
10. Jacques, J. Compt. Rend. Acad. Sci., Ser. IIc: Chim. 1999,
2, 181–183.
11. Sustmann, R.; Altevogt, R. Tetrahedron Lett. 1981, 22,
5167–5170.
12. Spectral data for new compounds, 5: 1H NMR (400
MHz, CDCl3) l 0.77–0.85 (m, 2H), 1.34–1.48 (m, 2H),
13. Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995,
117, 5973–5982.