1478
J. S. Yadav et al. / Tetrahedron Letters 51 (2010) 1475–1478
Kumar, G. G. K. S.; Reddy, M. G. Tetrahedron Lett. 2007, 48, 4903–4906; (d) Yadav,
Ph), 6.08 (d, 1H, J = 3.7 Hz, C1H), 4.72 (d, 1H, J = 3.7 Hz, C2H), 4.56 (ddd, 1H,
J = 3.4, 4.5, 12.3, C5H), 4.38 (dd, 1H, J = 1.7, 11.7 Hz, C4H), 4.37 (dd, 1H, J = 1.7,
11.7 Hz, C7H), 4.19 (d, 1H, J = 1.7 Hz, C3H), 2.56 (q, 1H, J = 12.4 Hz, C6H), 2.29
(ddd, 1H, J = 1.7, 4.3, 12.2, C0 H), 1.54 (s, 3H, CH3), 1.33 (s, 3H, CH03). 13C NMR
(CDCl3, 150 MHz): d 19.1, 266.1, 26.6, 40.5, 79.3, 79.7, 84.8, 100.0, 104.7, 125.8,
128.4, 128.5, 128.5, 130.1, 133.7, 172.0. ESI-MS: m/z: 402 (M+H). (3c): White
J. S.; Kumar, N. N.; Reddy, M. S.; Prasad, A. R. Tetrahedron 2007, 63, 2689–2694;
(e) Yadav, J. S.; Reddy, B. V. S.; Maity, T.; Narayana Kumar, G. G. K. S. Tetrahedron
Lett. 2007, 48, 7155–7159; (f) Yadav, J. S.; Reddy, B. V. S.; Maity, T.; Narayana
Kumar, G. G. K. S. Tetrahedron Lett. 2007, 48, 8874–8877; (g) Yadav, J. S.; Reddy,
B. V. S.; Aravind, S.; Narayana Kumar, G. G. K. S.; Madhavi, C.; Kunwar, A. C.
Tetrahedron 2008, 64, 3025–3031; (h) Yadav, J. S.; Reddy, B. V. S.; Narayana
Kumar, G. G. K. S.; Aravind, S. Synthesis 2008, 48, 395–398.
solid, IR (neat):
m
3499, 2923, 2853, 1730, 1673, 1601, 1431, 1379, 1266, 1215,
1094, 1020, 966, 871, 791, 725 cmꢁ1
.
1H NMR (CDCl3, 500 MHz): d 7.32–7.24 (m,
5. (a) Miranda, P. O.; Diaz, D. D.; Padron, J. I.; Bermejo, J.; Martin, V. S. Org. Lett.
2003, 5, 1979–1982; (b) Miranda, P. O.; Diaz, D. D.; Padron, J. I.; Ramirez, M. A.;
Martin, V. S. J. Org. Chem. 2005, 70, 57–62.
4H Ph), 6.20 (d, 1H, J = 3.9 Hz), 4.77 (d, 1H, J = 2.9 Hz), 4.50 (ddd, 1H, J = 3.9, 7.8,
12.6 Hz), 4.30–4.38(q, 2H, J = 13.6, Hz), 4.11 (s, 1H), 2.41–2.48 (q, 1H,
J = 12.6 Hz), 2.29 (dd, 1H, J = 3.9, 8.7 Hz), 1.54 (s, 3H, CH3), 1.33 (s, 3H, CH3).
13C NMR (CDCl3, 75 MHz): d 18.3, 29.6, 40.1, 79.2, 78.7, 85.5, 105.0, 105.1, 114.2,
123.7, 124.4, 125.8, 126.3, 128.2, 129.7, 129.6. ESI-MS: m/z: 475 (M+K). (3d):
6. (a) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997,
62, 3426–3427; (b) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993–
995; (c) Dobbs, A. P.; Martinovic, S. Tetrahedron Lett. 2002, 43, 7055–7057; (d)
Dobbs, A. P.; Guesne, S. J. J.; Martinovic, S.; Coles, S. J.; Hursthouse, M. B. J. Org.
Chem. 2003, 68, 7880–7883; (e) Meilert, K.; Brimble, M. A. Org. Lett. 2005, 7,
3497–3500; (f) Miranda, P. O.; Ramirez, M. A.; Martin, V. S.; Padron, J. I. Org. Lett.
2006, 8, 1633–1636; (g) Leon, L. G.; Miranda, P. O.; Martin, V. S.; Padron, J. I.;
Padron, J. M. Bioorg. Med. Chem. Lett. 2007, 17, 3087–3090.
7. Typical procedure: A mixture of homoallylic alcohol (0.312 g, 2 mmol), aldehyde
(0.2 g, 1.2 mmol), and iodine (0.127 g, 1 mmol) in dichloromethane (5 mL) was
stirred at 23 °C for the specified amount of time (Table 1). After completion of
the reaction as indicated by TLC, the reaction was quenched with water and
extracted with ether (2 ꢀ 10 mL). The combined organic layers were washed
with aq sodium thiosulfate and brine, and dried over anhyd Na2SO4. Removal of
the solvent followed by purification on silica gel (Merck, 100–200 mesh, ethyl
acetate–hexane, 0.5–9.5) gave the pure tetrahydropyran. The products thus
obtained were characterized by IR, NMR, and mass spectroscopy. (3b) IR (neat):
White solid, IR (neat):
m
3437, 2922, 2853, 1600, 1503, 1457, 1376, 1245, 1161,
1085, 1016, 859 cmꢁ1
.
1H NMR (CDCl3, 300 MHz): d 1.37 (s, 6H), 2.31 (ddd, 1H,
J = 5.0, 6.9, 2.2 Hz), 2.71 (q, 1H, J = 12.8 Hz), 4.16 (s, 1H), 4.32, (s, 1H), 4.44–4.57
(m, 2H), 4.67 (d, 1H, J = 3.5 Hz), 6.01 (d, 1H, J = 3.5 Hz), 6.58 (s, 1H, Ph), 6.80 (t,
1H, J = 5.6 Hz), 6.94 (d, 1H, J = 6.2 Hz), 7.11–7.17 (m, 1H), 9.80 (s, 1H, OH). 13C
NMR (CDCl3, 150 MHz): d 14.1, 17.3, 26.1, 26.5, 29.7, 38.4, 53.4, 79.5, 79.8, 84.6,
96.1, 104.5, 112.2, 117.0, 120.3, 126.7, 129.6. ESI-MS: m/z: 441 (M+ Na). (3i):
White solid, IR (neat):
m 2964, 2926, 1734, 1468, 1367, 1274, 1099, 1022, 870,
797, 682 cmꢁ1 1H NMR (CDCl3, 300 MHz): d 0.82–0.92 (m, 12H methyl), 2.02 (q,
.
1H, J = 4.9, 6.2 Hz), 2.16 (dd, 1H, J = 3.9,5.2 Hz), 2.96 (q, 1H, J = 4.9, 5.8 Hz), 3.38
(q, 1H, J = 4.9 Hz), 3.95 (d, 1H, J = 16.2 Hz), 4.28 (m, 1H), 4.42 (d, 1H, J = 3.7 Hz),
4.62 (d, 1H, J = 4.9 Hz), 5.85 (d, 1H, J = 3.9 Hz). 13C NMR (CDCl3, 75 MHz): d 18.0,
20.4, 22.6, 29.6, 31.8, 32.4, 35.6, 79.2, 79.4, 82.8, 85.3, 104.2, 108.7. ESI-MS: m/z:
407 (M+K).
8. (a) Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960–
4961; (b) Ramesh, J.; Rychnovsky, S. D. Org. Lett. 2006, 8, 2175–2178; (c)
Biermann, U.; Lutzen, A.; Metzger, J. O. Eur. J. Org. Chem. 2006, 2631–2637.
m
3449, 3033, 2959, 2925, 2855, 1732, 1603, 1495, 1455, 1377, 1262, 1216, 1142,
1090, 1019, 860, 798, 699 cmꢁ1 1H NMR (600 MHz, CDCl3): d 7.38–7.28 (m, 5H,
.