8676
S. Yamada, I. Jahan / Tetrahedron Letters 46 (2005) 8673–8676
3. (a) Reebye, P. N.; Yiptong, C.; Samsoon, J.; Schulsinger,
2003, 44, 7429–7432; (d) Chang, M.-Y.; Chen, C.-Y.; Tasi,
M.-R.; Tseng, T.-W.; Chang, N.-C. Synthesis 2004, 840–
846; (e) Shih, K.-S.; Liu, C.-W.; Hsieh, Y.-J.; Chen, S.-F.;
Ku, H.; Liu, L. T.; Lin, Y.-C.; Huang, H.-L.; Wang, C.-L.
W. Heterocycles 1999, 51, 2439–2444; (f) Engelstoft, M.;
Hansen, J. B. Acta Chem. Scand. 1996, 50, 164–169.
11. Christensen, J. A.; Engelstoft, M.; Schaumburg, K.;
Schou, H.; Watjen, F. Tetrahedron Lett. 1983, 24, 5151–
5152.
F.; Fabricius, J. Pharmacopsychiatry 1982, 15, 164–169;
(b) Boerup, C.; Peterson, I. M.; Honore, P. F.; Wetter-
berg, L. Psychopharmacology 1979, 63, 241–243.
4. (a) Igarashi, J.; Ishiwata, H.; Kobayashi, Y. Tetrahedron
Lett. 2004, 45, 8065–8068; (b) Taylor, M. S.; Jacobsen, E.
N. J. Am. Chem. Soc. 2003, 125, 11204–11205; (c) Liu, L.
T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L.
J.; Wen, Y.-S. Tetrahedron: Asymmetry 2001, 12, 419–426;
(d) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M.
D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689–11698;
(e) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem.
Soc. 2001, 123, 1004–1005; (f) Amat, M.; Bosch, J.;
Hidalgo, J.; Canto, M.; Perez, M.; Llor, N.; Molins, E.;
Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000,
65, 3074–3084; (g) Yu, M. S.; Lantos, I.; Peng, Z.-Q.; Yu,
J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647–5651.
5. (a) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R.
Eur. J. Org. Chem. 2002, 3543–3551; (b) Cossy, J.;
Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetra-
hedron Lett. 2001, 42, 5705–5707.
12. Yamada, S.; Misono, T.; Ichikawa, M.; Morita, C.
Tetrahedron 2001, 57, 8939–8949.
27
13. Compound 2b: ½aꢁD ꢀ216.6 (c 0.54, MeOH); IR (neat):
1
3064, 1717, 1695, 1557, 1473 cmꢀ1; H NMR (400 MHz,
CDCl3): d 7.92 (s, 1H), 7.65–6.88 (m, 15H), 5.24–
5.23 (m, 2H), 4.75 (d, 1H, J = 4.4 Hz), 3.39 (dd, 1H,
J = 7.4, 11.0 Hz), 3.18 (dd, 1H, J = 6.4, 11.0 Hz); 13C
NMR (100 MHz, CDCl3): d 200.5, 169.9, 167.5, 162.9,
160.3, 139.6, 138.0, 137.0, 131.9, 131.8, 128.8, 128.8, 128.7,
128.6, 126.4, 120.3, 115.4, 115.2, 113.9, 71.5, 38.9, 38.1;
HRMS: calcd for C28H21N2O2FS2: 500.1029, found:
500.1092.
6. (a) Hughes, G.; Kimura, M.; Buchwald, S. L. J. Am. Chem.
Soc. 2003, 125, 11253–11258; (b) Murthy, K. S. K.; Rey, A.
W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355–5358;
(c) Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R.
New J. Chem. 2003, 27, 475–482; (d) Cossy, J.; Mirguet, O.;
Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001,
42, 7805–7807; (e) Senda, T.; Ogasawara, M.; Hayashi, T.
J. Org. Chem. 2001, 66, 6852–6856.
14. Yamada, S.; Misono, T.; Tsuzuki, S. J. Am. Chem. Soc.
2004, 126, 9862–9872.
15. AM1 calculations were performed by using Spartan 04ꢀ.
27
16. Compound 8: Mp 145–147 °C; ½aꢁD +72.6 (c 0.38,
MeOH); IR (KBr): 3448, 3032, 1668, 1601, 1345, 1263,
;
1229, 1257, 1114, 1028, 835, 754 cmꢀ1 1H NMR
(400 MHz, CDCl3): d 7.11 (dd, J = 5.4, 8.4 Hz, 2H), 6.99
(t, J = 8.4 Hz, 2H), 4.39 (d, J = 13.6 Hz, 1H), 4.29 (br d,
J = 10.4 Hz, 1H), 3.40 (br s, 1H), 3.17–3.14 (m, 1H), 3.04
(dt, J = 4.2, 13.0 Hz, 1H), 3.00–2.86 (m, 2H), 2.11 (br s,
1H), 2.02–1.88 (ddd, J = 4.6, 13.0, 26.0 Hz, 1H), 1.65 (br
d, J = 10.8 Hz, 1H), 1.49 (s, 9H); 13C NMR (100 MHz,
CDCl3): d 162.5, 160.0, 135.5, 128.3, 128.2, 115.2, 115.0,
80.5, 57.7, 45.5, 42.6, 28.4, 25.2.
7. (a) Gill, C. D.; Greenhalgh, D. A.; Simpkins, N. S.
Tetrahedron 2003, 59, 9213–9230; (b) Greenhalgh, D. A.;
Simpkins, N. S. Synlett 2002, 2074–2076.
8. (a) De Gonzalo, G.; Brieva, R.; Sanchez, V. M.; Bayod,
M.; Gotor, V. Tetrahedron: Asymmetry 2003, 14, 1725–
1731; (b) de Gonzalo, G.; Brieva, R.; Sanchez, V. M.;
Bayod, M.; Gotor, V. J. Org. Chem. 2003, 68, 3333–3336;
(c) Palomo, J. M.; Fernandez-Lorente, G.; Mateo, C.;
Fuentes, M.; Guisan, J. M.; Fernandez-Lafuente, R.
Tetrahedron: Asymmetry 2002, 13, 2653–2659; (d) Palomo,
J. M.; Fernandez-Lorente, G.; Mateo, C.; Fernandez-
Lafuente, R.; Guisan, J. M. Tetrahedron: Asymmetry
2002, 13, 2375–2381; (e) de Gonzalo, G.; Brieva, R.;
Sanchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001,
66, 8947–8953.
9. (a) Czibula, L.; Nemes, A.; Seboek, F.; Szantay, C., Jr.;
Mak, M. Eur. J. Org. Chem. 2004, 3336–3339; (b) Sugi,
K.; Itaya, N.; Katsura, T.; Igi, M.; Yamazaki, S.;
Ishibashi, T.; Yamaoka, T.; Kawada, Y.; Tagami, Y.;
Otsuki, M.; Ohshima, T. Chem. Pharm. Bull. 2000, 48,
529–536.
17. Crystal data and structure refinement for 8: Data were
collected on a RigakuAFC7R diffractometer with Cu-K a
˚
radiation (k = 1.54178 A). The structures were solved
by direct methods with SHELXS-93 and refined by full-
matrix least-squares on F2 using SHELXL-97. Compound
8: C17H24NO3F, M = 309.37, monoclinic, P21, l =
0.735 mmꢀ1
,
˚
a = 11.740(3),
b = 9.615(2),
c =
3
˚
7.6352(13) A, b = 99.36(2), V = 850.4(3) A , T = 296 K,
Z = 2, Dc = 1.208 g cmꢀ1. A total of 2548 reflections were
collected and 1988 are unique (Rint = 0.0222). R1 and wR2
are 0.0398 [I > 2r(I)] and 0.1393 (all data), respectively.
Crystallographic data (excluding structure factors) for the
structures in this letter have been deposited with the
Cambridge Crystallographic Data Centre as supplemen-
tary publication numbers CCDC 282601. Copies of the
data can be obtained, free of charge, on application to
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax:
+44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.jp].
10. ( )-Paroxetine: (a) Takasu, K.; Nishida, N.; Tomimura,
A.; Ihara, M. J. Org. Chem. 2005, 70, 3957–3962; (b)
Chen, C.-Y.; Chang, B.-R.; Tsai, M.-R.; Chang, M.-Y.;
Chang, N.-C. Tetrahedron 2003, 59, 9383–9387; (c)
Takasu, K.; Nishida, N.; Ihara, M. Tetrahedron Lett.
´
´
18. Plenge, P.; Mellerup, E. T.; Honore, T.; Honore, P. F.
J. Pharm. Pharmacol. 1987, 39, 877–882.