B. V. Subba Reddy et al. / Tetrahedron Letters 51 (2010) 6511–6515
6515
5
.
.
(a) Yadav, J. S.; Padmavani, B.; Reddy, B. V. S.; Venugopal, C.; Rao, A. B. Synlett
007, 2045; (b) Yadav, J. S.; Thrimurtulu, N.; Gayathri, K. U.; Reddy, B. V. S.;
304, 85; (d) Kumar, A.; Srivastava, S.; Gupta, G. Tetrahedron Lett. 2010, 51, 517;
(e) Kumar, A.; Gupta, G.; Srivastava, S. J. Comb. Chem. 2010, 12, 458.
11. General procedure: A mixture of carbonyl compound or epoxide (1 mmol),
2
Prasad, A. R. Tetrahedron Lett. 2008, 49, 6617; (c) Yadav, J. S.; Lakshmi, K. A.;
Reddy, N. M.; Prasad, A. R.; Reddy, B. V. S. Tetrahedron 2010, 44, 334.
(a) Snider, B. B.; Hawryluk, N. Org. Lett. 2000, 2, 635; (b) Michelet, V.; Genet, J.-
P. Curr. Org. Chem. 2005, 9, 405; (c) Suhara, Y.; Yamaguchi, Y.; Collins, B.;
Schnaar, R. L.; Yanagishita, M.; Hildreth, J. E. K.; Shimada, I.; Ichikawa, Y. Bioorg.
Med. Chem. 2002, 10, 1999; (d) Hofle, G.; Steimnetz, H.; Gerth, K.; Reichenbach,
H. Liebigs. Ann. Chem. 1991, 941; (e) Yadav, J. S.; Narayana Kumar, G. G. K. S.
Tetrahedron 2010, 66, 480; (f) Ferrie, L.; Remond, S.; Capdevielle, P.; Cossy, J.
Org. Lett. 2007, 9, 2641.
3
homoallylic alcohol (1 mmol), and cellulose-SO H (70 mg) in nitromethane
(5 mL) was stirred at room temperature for a specified time (Tables 1 and 2).
After completion of the reaction, as indicated by TLC, the catalyst was removed
6
2 4
by filteration and the resulting filtrate was dried over Na SO and concentrated
under vacuum. The product was purified by silica gel column chromatography
(70:30, hexane/ethyl acetate) to afford the pure tetrahydropyran-4-ol. The
products thus obtained were characterized by IR, NMR, and mass spectroscopy.
The spectral data were found to be consistent with authentic samples.7
7
.
(a) Zhang, W. C.; Viswanathan, G. S.; Li, C. J. J. Chem. Soc., Chem.Commun. 1999,
Compound 3h: (E)-2-styryl-tetrahydro-2H-pyran-4-ol: IR (KBr):
2853, 1601, 1449, 1203, 1138, 1074, 967, 747 cm . H NMR (300 MHz, CDCl ): d
m
3387, 2924,
À1
1
2
91; (b) Zhang, W. C.; Li, C. J. Tetrahedron 2000, 56, 2403; (c) Yadav, J. S.; Subba
3
Reddy, B. V.; Kumar, G. M.; Murthy, C. V. S. R. Tetrahedron Lett. 2001, 42, 89; (d)
Keh, C. C. K.; Namboodiri, V. V.; Varma, R. S.; Li, C. J. Tetrahedron Lett. 2002, 43,
7.15–7.42 (m, 5H), 6.55 (dd, 1H, J = 1.5, 15.8 Hz) 6.14 (dd, 1H, J = 6.0, 15.8 Hz),
4.04–411 (m, 1H), 3.77–3.95 (m, 2H), 3.42–3.51 (m, 1H), 2.02–2.10 (m, 1H),
4
993; (e) Yadav, J. S.; Subba Reddy, B. V.; Narayana Kumar, G. G. K. S.; Aravind,
S. Synthesis 2008, 48, 395; (f) Tadpetch, K.; Rychnovsky, S. D. Org. Lett. 2008, 10,
839.
1.86–1.93 (m, 1H), 1.32–1.61 (m, 2H). 13C NMR (75 MHz, CDCl
): d 136.5, 130.4,
3
+
129.3, 128.4, 127.6, 126.4, 76.4, 67.8, 65.8, 41.4, 35.2. LC–MS: m/z: (M ) 204.
HRMS calcd for C13 : 204.1150. Found: 204.1156.
Compound 5a: 2-benzyltetrahydro-2H-pyran-4-ol: IR (KBr):
4
16 2
H O
8
9
.
.
Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171.
m
3414, 2924, 1603,
À1
1
(a) Niknam, K.; Saberi, D.; Sefat, M. N. Tetrahedron Lett. 2010, 51, 2959; (b)
Paolis, O. D.; Teixeira, L.; Török, B. Tetrahedron Lett. 2009, 50, 2939; (c) Saidi, M.
R.; Torkiyan, L.; Azizi, N. Org. Lett. 2006, 8, 2079; (d) Rafiee, E.; Jafari, H. Bioorg.
Med. Chem. Lett. 2006, 16, 2463.
0. (a) Ahmad, S.; Ali, M. Appl. Catal., A 2007, 331, 149; (b) Shaabani, A.; Rahmati,
A.; Badri, Z. Catal. Commun. 2008, 9, 13; (c) Madhav, J. V.; Reddy, Y. T.; Reddy, P.
N.; Reddy, M. N.; Kuarm, S.; Crooks, P. A.; Rajitha, B. J. Mol. Catal. A: Chem. 2009,
1493, 1249, 1067, 755, 700 cm . H NMR (300 MHz, CDCl ): d 7.15–7.33 (m, 5H)
3
3.99 (dd, 1H, J = 4.0, 11.7 Hz) 3.52–3.78 (m, 1H) 3.29–3.48 (m, 2H) 2.62–2.94 (m,
2H), 1.80–1.92 (m, 2H) 1.41–1.54 (m, 1H), 1.18–1.33 (m, 1H). 1 C NMR (75 MHz,
3
CDCl
3
): d 138.0, 129.2, 128.2, 127.8, 77.0, 67.9, 65.8, 42.5, 40.7, 35.5. LC–MS: m/z:
+
1
(M ) 192. HRMS calcd for C12 : 192.1150. Found: 192.1148.
16 2
H O
12. (a) Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960; (b)
Ramesh, J.; Rychnovsky, S. D. Org. Lett. 2006, 8, 2175.