LETTER
[2+3] Cycloaddition between Substituted Phenols and Allylsilane
1079
Tohma, H.; Kita, Y. J. Org. Chem. 1998, 63, 7698.
1 H, J = 15.4, 8.2 Hz), 1.30 (dd, 1 H, J = 14.3, 6.6 Hz), 1.09
(dd, 1 H, J = 14.3, 8.8 Hz), 0.09 (s, 9 H). 13C NMR (75 MHz,
CDCl3): d = 158.0, 129.4, 127.6, 124.8, 118.4, 110.0, 82.9,
38.1, 25.1, –0.8.
(h) Arisawa, M.; Utsumi, S.; Nakajima, M.; Ramesh, N. G.;
Tohma, H.; Kita, Y. Chem. Commun. 1999, 469. (i)Tohma,
H.; Morioka, H.; Takizawa, S.; Arisawa, M.; Kita, Y.
Tetrahedron 2001, 57, 345. (j) Hamamoto, H.; Anilkumar,
G.; Tohma, H.; Kita, Y. Chem. Eur. J. 2002, 8, 5377.
(6) (a) Braun, N. A.; Ciufolini, M. A.; Peters, K.; Peters, E.-M.
Tetrahedron Lett. 1998, 39, 4667. (b) Braun, N. A.; Bray, J.;
Ousmer, M.; Peters, K.; Peters, E.-M.; Bouchu, D.;
Ciufolini, M. A. J. Org Chem. 2000, 65, 4397. (c) Ousmer,
M.; Braun, N. A.; Bavoux, C.; Perrin, M.; Ciufolini, M. A. J.
Am. Chem. Soc. 2001, 123, 7534. (d) Canesi, S.; Belmont,
P.; Bouchu, D.; Rousset, L.; Ciufolini, M. A. Tetrahedron
Lett. 2002, 43, 5193. (e) Canesi, S.; Bouchu, D.; Ciufolini,
M. A. Angew. Chem. Int. Ed. 2004, 43, 4336; Angew. Chem.
2004, 116, 4436. (f) Peuchmaur, M.; Wong, Y.-S. J. Org
Chem. 2007, 72, 5374.
Entry 4: 1H NMR (300 MHz, CDCl3): d = 7.41 (d, 1 H, J =
1.7 Hz), 7.36 (dd, 1 H, J = 8.2, 1.7 Hz), 6.51 (d, 1 H, J = 8.2
Hz), 4.92 (m, 1 H), 3.26 (dd, 1 H, J = 15.4, 8.2 Hz), 2.77 (dd,
1 H, J = 15.4, 8.2 Hz), 1.29 (dd, 1 H, J = 14.3, 6.6 Hz), 1.07
(dd, 1 H, J = 14.3, 8.8 Hz), 0.08 (s, 9 H). 13C NMR (75 MHz,
CDCl3): d = 159.3, 136.6, 133.5, 130.4, 111.5, 82.8, 37.8,
25.1, –0.9.
Entry 5: 1H NMR (300 MHz, CDCl3): d = 6.71 (s, 1 H), 6.62
(d, 1 H, J = 8.2 Hz), 6.58 (d, 1 H, J = 8.2 Hz), 4.85 (m, 1 H),
3.71 (s, 3 H), 3.21 (dd, 1 H, J = 15.4, 8.2 Hz), 2.74 (dd, 1 H,
J = 15.4, 8.2 Hz), 1.28 (dd, 1 H, J = 14.3, 6.6 Hz), 1.07 (dd,
1 H, J = 14.3, 8.8 Hz), 0.07 (s, 9 H). 13C NMR (75 MHz,
CDCl3): d = 153.7, 128.3, 113.1, 112.5, 111.3, 108.9, 82.3,
56.0, 38.6, 25.1, –0.8.
(7) (a) Akai, S.; Kawashita, N.; Morita, N.; Nakamura, Y.; Iio,
K.; Kita, Y. Heterocycles 2002, 58, 75. (b) Zawada, P. V.;
Banfield, S. C.; Kerr, M. A. Synlett 2003, 971.
Entry 6: 1H NMR (300 MHz, CDCl3): d = 7.01 (d, 1 H, J =
1.7 Hz), 6.94 (dd, 1 H, J = 8.2, 1.7 Hz), 6.67 (d, 1 H, J = 8.2
Hz), 4.91 (m, 1 H), 3.81 (t, 2 H, J = 6.4 Hz), 3.26 (dd, 1 H,
J = 15.4, 8.2 Hz), 2.79 (m, 3 H), 1.33 (dd, 1 H, J = 14.3, 6.6
Hz), 1.09 (dd, 1 H, J = 14.3, 8.8 Hz), 0.10 (s, 9 H). 13C NMR
(75 MHz, CDCl3): d = 158.1, 129.7, 128.3, 127.8, 125.4,
109.0, 82.3, 63.9, 38.5, 38.2, 25.2, –0.8.
(8) Kita, Y.; Tohma, H.; Kikuchi, K.; Inagaki, M.; Yakura, T. J.
Org. Chem. 1991, 56, 435.
(9) TFE (pKa ca. 12.4, nucleophilicity ca. –2.8); HFIP (pKa ca.
9.3, nucleophilicity ca. –4.2).
(10) (a) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem.
Int. Ed. 2000, 39, 4593. (b) Drutu, I.; Njardarson, J. T.;
Wood, J. L. Org. Lett. 2002, 4, 493. (c) Canesi, S.; Bouchu,
D.; Ciufolini, M. A. Org. Lett. 2005, 7, 175. (d) Ciufolini,
M. A.; Canesi, S.; Ousmer, M.; Braun, N. A. Tetrahedron
2006, 62, 5318.
(11) Jean, A.; Cantat, J.; Bérard, D.; Bouchu, D.; Canesi, S. Org.
Lett. 2007, 9, 2553.
(12) Bérard, D.; Jean, A.; Canesi, S. Tetrahedron Lett. 2007, 48,
8238.
(13) (a) Wang, S.; Gates, B. D.; Swenton, J. S. J. Org. Chem.
1991, 56, 1979. (b) Juhasz, L.; Kuerti, L.; Antus, S. J. Nat.
Prod. 2000, 63, 866.
(14) Quideau, S.; Looney, M. A.; Pouységu, L. Org. Lett. 1999,
1, 1651.
(15) (a) Quideau, S.; Pouységu, L.; Looney, M. A. J. Org. Chem.
1998, 63, 9597. (b) Quideau, S.; Pouységu, L.; Oxoby, M.;
Looney, M. A. Tetrahedron 2001, 57, 319. (c) Lebrasseur,
N.; Fan, G. J.; Oxoby, M.; Looney, M. A.; Quideau, S.
Tetrahedron 2005, 61, 1551. (d) Ozanne-Beaudenon, A.;
Quideau, S. Angew. Chem. Int. Ed. 2005, 44, 7065.
(e) Nicolaou, K. C.; Edmonds, D. J.; Li, A.; Tria, G. S.
Angew. Chem. Int. Ed. 2007, 119, 4016.
Entry 7: 1H NMR (300 MHz, CDCl3): d = 7.68 (d, 2 H, J =
8.2 Hz), 7.29 (d, 2 H, J = 8.2 Hz), 6.85 (d, 1 H, J = 1.7 Hz),
6.76 (dd, 1 H, J = 8.2, 1.7 Hz), 6.60 (d, 1 H, J = 8.2 Hz), 4.89
(m, 1 H), 4.40 (t, 1 H, J = 6.6 Hz), 3.21 (dd, 1 H, J = 15.4,
8.2 Hz), 3.15 (q, 2 H, J = 6.6 Hz), 2.74 (dd, 1 H, J = 15.4, 8.2
Hz), 2.66 (t, 2 H, J = 6.6 Hz), 2.42 (s, 3 H), 1.31 (dd, 1 H,
J = 14.3, 6.6 Hz), 1.09 (dd, 1 H, J = 14.3, 8.8 Hz), 0.09 (s, 9
H). 13C NMR (75 MHz, CDCl3): d = 158.3, 143.3, 136.8,
129.6, 128.8, 128.0, 127.9, 127.0, 125.1, 109.1, 82.4, 44.5,
38.1, 35.0, 25.2, 21.5, –0.9.
Entry 8: 1H NMR (300 MHz, CDCl3): d = 7.31 (d, 1 H, J =
1.7 Hz), 7.27 (dd, 1 H, J = 8.2, 1.7 Hz), 6.76 (d, 1 H, J = 8.2
Hz), 4.92 (m, 1 H), 3.29 (dd, 1 H, J = 15.4, 8.2 Hz), 2.81 (dd,
1 H, J = 15.4, 8.2 Hz), 1.34 (dd, 1 H, J = 14.3, 6.6 Hz), 1.11
(dd, 1 H, J = 14.3, 8.8 Hz), 0.24 (s, 9 H), 0.11 (s, 9 H). 13
NMR (75 MHz, CDCl3): d = 160.2, 133.3, 130.5, 129.7,
127.0, 108.9, 82.2, 38.0, 25.3, –0.7.
C
Entry 9: 1H NMR (300 MHz, CDCl3): d = 7.29 (t, 2 H, J =
8.2 Hz), 7.02 (t, 1 H, J = 8.2 Hz), 6.94 (d, 2 H, J = 8.2 Hz),
6.85 (d, 1 H, J = 1.7 Hz), 6.79 (dd, 1 H, J = 8.2, 1.7 Hz), 6.68
(d, 1 H, J = 8.2 Hz), 4.93 (m, 1 H), 3.26 (dd, 1 H, J = 15.4,
8.2 Hz), 2.79 (dd, 1 H, J = 15.4, 8.2 Hz), 1.34 (dd, 1 H, J =
14.3, 6.6 Hz), 1.13 (dd, 1 H, J = 14.3, 8.8 Hz), 0.10 (s, 9 H).
13C NMR (75 MHz, CDCl3): d = 158.8, 155.7, 149.6, 129.4,
128.7, 122.0, 119.3, 117.3, 117.0, 109.3, 82.7, 38.4, 25.2,
–0.8.
(16) Reaction effected with HFIP as solvent is easier to purify by
chromatography than with TFE as solvent.
(17) NMR Data (Table 1)
Entry 1: 1H NMR (300 MHz, CDCl3): d = 7.31 (d, 1 H, J =
1.7 Hz), 7.27 (dd, 1 H, J = 8.2, 1.7 Hz), 6.76 (d, 1 H, J = 8.2
Hz), 4.92 (m, 1 H), 3.29 (dd, 1 H, J = 15.4, 8.2 Hz), 2.81 (dd,
1 H, J = 15.4, 8.2 Hz), 1.34 (dd, 1 H, J = 14.3, 6.6 Hz), 1.11
(18) NMR Data
Compound 13: 1H NMR (300 MHz, CDCl3): d = 7.76 (d, 1
H, J = 8.2 Hz), 7.63 (d, 1 H, J = 8.2 Hz), 7.54 (d, 1 H, J = 8.2
Hz), 7.43 (t, 1 H, J = 8.2 Hz), 7.27 (d, 1 H, J = 8.2 Hz), 7.05
(d, 1 H, J = 8.2 Hz), 5.10 (m, 1 H), 3.56 (dd, 1 H, J = 14.8,
8.8 Hz), 3.03 (dd, 1 H, J = 14.8, 8.2 Hz), 1.37 (dd, 1 H, J =
13.7, 6.6 Hz), 1.18 (dd, 1 H, J = 14.3, 8.8 Hz), 0.11 (s, 9 H).
13C NMR (75 MHz, CDCl3): d = 156.8, 130.8, 128.9, 128.7,
128.6, 126.4, 122.5, 122.5, 118.5, 112.1, 82.9, 36.9, 25.6,
–0.7.
(dd, 1 H, J = 14.3, 8.8 Hz), 0.24 (s, 9 H), 0.11 (s, 9 H). 13
NMR (75 MHz, CDCl3): d = 156.8, 130.8, 128.7, 128.6,
126.4, 122.5, 122.5, 118.5, 112.1, 82.9, 36.9, 25.6, –0.7.
C
Entry 2: 1H NMR (300 MHz, CDCl3): d = 7.32 (d, 1 H, J =
1.7 Hz), 7.08 (dd, 1 H, J = 8.2, 1.7 Hz), 6.66 (d, 1 H, J = 8.2
Hz), 4.90 (m, 1 H), 3.26 (dd, 1 H, J = 15.4, 8.2 Hz), 2.82 (dd,
1 H, J = 15.4, 8.2 Hz), 1.26 (m + s, 4 H), 1.05 (dd, 1 H, J =
14.3, 8.8 Hz), 0.09 (s, 9 H). 13C NMR (75 MHz, CDCl3): d =
158.0, 129.4, 127.6, 124.8, 118.4, 110.0, 82.9, 38.1, 25.1,
–0.8.
Compound 15: 1H NMR (300 MHz, CDCl3): d = 6.35 (s, 2
H), 4.92 (m, 1 H), 3.84 (s, 3 H), 3.77 (s, 3 H), 3.22 (dd, 1 H,
J = 15.4, 8.2 Hz), 2.79 (dd, 1 H, J = 15.4, 8.2 Hz), 1.42 (dd,
1 H, J = 14.3, 6.6 Hz), 1.19 (dd, 1 H, J = 14.3, 8.8 Hz), 0.10
(s, 9 H). 13C NMR (75 MHz, CDCl3): d = 154.4, 144.3,
141.9, 128.3, 101.4, 99.1, 82.9, 56.0, 38.9, 30.9, 25.0, –0.9.
Entry 3: 1H NMR (300 MHz, CDCl3): d = 7.23 (d, 1 H, J =
1.7 Hz), 7.18 (dd, 1 H, J = 8.2, 1.7 Hz), 6.60 (d, 1 H, J = 8.2
Hz), 4.93 (m, 1 H), 3.27 (dd, 1 H, J = 15.4, 8.2 Hz), 2.79 (dd,
Synlett 2008, No. 7, 1076–1080 © Thieme Stuttgart · New York