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D. Chikkanna, H. Han
LETTER
(3) (a) Han, H.; Cho, C. W.; Janda, K. D. Chem.–Eur. J. 1999,
5, 1565. (b) Singh, O. V.; Han, H. Tetrahedron Lett. 2003,
44, 2387. (c) Singh, O. V.; Han, H. Tetrahedron Lett. 2003,
44, 5289.
(10) (a) Wang, Y.-F.; Takaoka, Y.; Wong, C.-H. Angew. Chem.,
Int. Ed. Engl. 1994, 33, 1242. (b) Fechter, M. H.; Stutz, A.
E. Carbohydr. Res. 1999, 319, 55.
(11) Hayes, P.; Suthers, B. D.; Kitching, W. Tetrahedron Lett.
2000, 41, 6175.
(4) For a review, see (a) Robin, S.; Rousseau, G. Tetrahedron
1998, 54, 13681. (b) Khalaf, J. F.; Datta, A. J. Org. Chem.
2004, 69, 387. (c) Enierga, G.; Espiritu, M.; Perlmutter, P.;
Pham, N.; Rose, M.; Sjoberg, S.; Thienthong, N.; Wong, K.
Tetrahedron: Asymmetry 2001, 12, 597. (d) Takahata, H.;
Bandoh, H.; Momose, T. Tetrahedron: Asymmetry 1991, 2,
351. (e) Takahata, H.; Banba, Y.; Tajima, M.; Momose, T. J.
Org. Chem. 1991, 56, 240. (f) Takahata, H.; Takehara, H.;
Ohkubo, N.; Momose, T. Tetrahedron: Asymmetry 1990, 1,
561. (g) Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem.
1988, 53, 5731. (h) Tokuda, M.; Yamada, Y.; Suginome, H.
Chem. Lett. 1988, 17, 1289. (i) Kinsman, R.; Lathbury, D.;
Vernon, P.; Gallagher, T. J. Chem. Soc., Chem. Commun.
1987, 243. (j) Harding, K. E.; Marman, T. H. J. Org. Chem.
1984, 49, 2838. (k) Harding, K. E.; Burks, S. R. J. Org.
Chem. 1984, 49, 40. (l) Harding, K. E.; Burks, S. R. J. Org.
Chem. 1981, 46, 3920.
(5) Singh, S.; Chikkanna, D.; Singh, O. V.; Han, H. Synlett
2003, 1279.
(6) The compound I was prepared from the reaction of ethyl 4-
bromocrotonate with p-methoxyphenol in the presence of
K2CO3 and a catalytic amount of 18-crown-6 in MeCN at r.t.
(yield: 80%).
(7) Takaku, H.; Kamaike, K.; Tsuchiya, H. J. Org. Chem. 1984,
49, 51.
(8) Burk, M. J.; Allen, J. G. J. Org. Chem. 1997, 62, 7054.
(9) (a) Mitsunobu, O. Synthesis 1981, 1. (b) Hughes, D. L. Org.
React. 1992, 42, 335.
(12) Fukuyama, T.; Laird, A. A.; Hotchkiss, L. M. Tetrahedron
Lett. 1985, 26, 6291.
(13) Compound 14: [a]D +20.0 (c 1.0, CHCl3). 1H NMR (500
MHz, CDCl3): d = 7.35–7.25 (5 H, m), 6.82–6.75 (4 H, m),
4.77–4.64 (1 H, m), 4.60–4.55 (2 H, m), 4.25 and 3.84 (1 H,
br s), 4.20–4.02 (5 H, m), 3.75 (3 H, s), 2.30 and 2.11 (1 H,
m,) 1.59 and 1.30 (1 H, t, J = 10.5 Hz), 1.44 and 1.40 (9 H,
s). 13C NMR (125 MHz, CDCl3): d = 154.0, 153.9, 152.8,
137.4, 128.6, 128.2, 127.8, 115.9, 114.6, 81.3, 80.9, 73.4,
71.6, 65.4, 56.7, 55.6, 55.3, 30.3, 28.4, minor peaks due to
rotational isomer(s): 81.0, 80.4, 73.7, 71.6, 70.8, 65.4, 64.1,
58.9, 54.6. Compound 16: [a]D +50.0 (c 1.0, CHCl3). 1H
NMR (500 MHz, CDCl3): d = 7.35–7.28 (5 H, m), 6.93 (2 H,
d, J = 9.0 Hz), 6.83 (2 H, d, J = 9.0 Hz), 4.71 (1 H, d,
J = 11.5 Hz), 4.67 (1 H, d, J = 11.5 Hz), 4.25–4.12 (6 H, m),
3.78–3.70 (1 H, m), 3.77 (3 H, s), 2.25 (1 H, dd, J = 11.5 and
6.0 Hz), 2.17 (1 H, dd, J = 11.5 and 4.5 Hz), 1.48 (9 H, s).
13C NMR (125 MHz, CDCl3): d = 155.1, 154.5, 151.9, 137.3,
128.5, 128.1, 127.9, 116.2, 114.7, 81.2, 77.1, 72.6, 70.9,
66.7, 60.1, 59.1, 55.7, 34.0, 28.5. Compound 17: [a]D +19.0
(c 1.0, CHCl3). 1H NMR (500 MHz, CDCl3): d = 7.40–7.20
(5 H, m), 6.85–6.70 (4 H, m), 4.72 (1 H, d, J = 11.5 Hz), 4.51
(1 H, d, J = 11.5 Hz), 4.50–4.35 (2 H, m), 4.25–4.10 (3 H,
m), 4.00 (1 H, br s), 3.71 (3 H, s), 1.91 (1 H, d, J = 12.0 Hz),
1.48 (1 H, d, J = 12.0 Hz), 1.32 (9 H, s). 13C NMR (75 MHz,
CDCl3): d = 154.8, 154.1, 152.0, 137.3, 128.5, 128.0, 127.7,
116.8, 114.6, 81.6, 75.9, 75.8, 71.4, 65.5, 65.4, 58.3, 55.6,
35.0, 28.4.
Synlett 2004, No. 13, 2311–2314 © Thieme Stuttgart · New York