Ethyl 5-(4-chlorophenyl)-5-(trifluoromethyl)-tetrahydrofuran-2-
W. R. Roush, Adv. Synth. Catal., 2004, 346, 1035; (d) X. Lu, Y. Du and
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5 For mechanisms, see: (a) T. Dudding, O. Kwon and E. Mercier, Org.
Lett., 2006, 8, 3643; (b) E. Mercier, B. Fonovic, C. Henry, O. Kwon and
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carboxylate (4ad). Colorless oil; Rf 0.4 (petroleum ether/ethyl
1
acetate = 20 : 1); H NMR (CDCl3, 300 MHz): d 7.56–7.46 (m,
2H), 7.39–7.33 (m, 2H), 4.67–4.62 (m, 1H), 4.33–4.20 (m, 2H),
2.78–2.69 (m, 1H), 2.39–2.15 (m, 3H), 1.32 (t, J = 7.2 Hz, 3H); 13
C
NMR (CDCl3, 75 MHz): d 170.9, 136.2, 135.0, 128.7, 128.2, 124.8
(q, J = 282 Hz), 86.9 (q, J = 29 Hz), 78.7, 61.5, 33.8, 29.4, 14.2;
IR (KBr): n 2983, 1757, 1612, 1584, 1513, 1464, 1375, 1302, 1252,
1174, 1094, 913, 832, 740 cm-1; HRMS (EI) calcd for C14H14ClF3O3
[M]+ 322.0584, found 322.0587.
Cyclohexyl
5-(thiophen-2-yl)-5-(trifluoromethyl)-tetrahydro-
6 For intramolecular version, see: (a) J.-C. Wang, S.-S. Ng and M. J.
Krische, J. Am. Chem. Soc., 2003, 125, 3682; (b) C. E. Henry and O.
Kwon, Org. Lett., 2007, 9, 3069.
furan-2-carboxylate (4af). Colorless oil; Rf 0.4 (petroleum
ether/ethyl acetate = 20 : 1); 1H NMR (CDCl3, 300 MHz): d 7.32
(dd, J1 = 5.1 Hz, J2 = 0.8 Hz, 1H), 7.10 (d, J = 3.6 Hz, 1H), 7.02
(dd, J1 = 5.1 Hz, J2 = 3.6 Hz, 1H), 4.90–4.81 (m, 1H), 4.75–4.72
(m, 1H), 2.73–2.63 (m, 1H), 2.44–2.26 (m, 3H), 1.89–1.84 (m,
2H), 1.76–1.73 (m, 2H), 1.55–1.26 (m, 6H); 13C NMR (CDCl3, 75
MHz): d 170.5, 141.6, 127.4, 126.4, 125.9 (q, J = 0.75 Hz), 124.4
(q, J = 282 Hz), 86.3 (q, J = 31 Hz), 79.2, 74.0, 34.9, 31.5 (q, J =
4.5 Hz), 29.5, 25.4, 23.7 (q, J = 2.3 Hz); IR (KBr): n 2938, 2859,
1732, 1594, 1455, 1177, 1082, 1014, 707 cm-1; HRMS (EI) calcd
for C16H19F3O3S [M]+ 348.1007, found 348.1011.
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Xu and X.-F. Lao, Chem. Commun., 1997, 79; (b) B. F. O’Donovan,
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2550.
Acknowledgements
8 For the asymmetric reactions, see: (a) G. Zhu, Z. Chen, Q. Jiang, D.
Xiao, X. Cao, P. Cao and X. Zhang, J. Am. Chem. Soc., 1997, 119,
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Am. Chem. Soc., 2011, 133, 1726.
Financial support from National Science Foundation of China
(20932008), the ministry of Science and Technology of China
(2011CB808600), and the Chinese Academy of Sciences is greatly
acknowledged.
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5264 | Org. Biomol. Chem., 2011, 9, 5260–5265
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