1960
M. S. Valle et al. / Tetrahedron Letters 49 (2008) 1957–1960
3
9, 3413–3416; (e) Miranda, P. C. M. L.; Correia, C. R. D. Tetrahedron
7. CCDC 670768 contains the supplementary crystallographic data for
Lett. 1999, 40, 7735–7738; (f) Oliveira, D. F.; Miranda, P. C. M. L.;
Correia, C. R. D. J. Org. Chem. 1999, 64, 6646–6652; (g) de Faria, A.
R.; Salvador, E. L.; Correia, C. R. D. J. Org. Chem. 2002, 67, 3651–
3
4
661; (h) de Oca, A. C. B. M.; Correia, C. R. D. Arkivoc 2003, 10, 390–
03; (i) Ambr o´ sio, J. C. L.; Santos, R. H. de A.; Correia, C. R. D. J.
8. Characterization data for 6 (HCl): Rf 0.10 (CH
2
ꢀ1
Cl
2
/MeOH/NH
4
OH
2
0
14:5:1); ½aꢁ +9.20 (c 0.5, H
2
O); IR (film, cm ): 3304, 2947 2284,
D
1
Braz. Chem. Soc. 2003, 14, 27–38.
2
1469, 1383, 1335, 1176, 1116, 1028, 903; H NMR (500 MHz, D O): d
4
. (a) Garcia, A. L. L.; Correia, C. R. D. Tetrahedron Lett. 2003, 44,
1.95 (m, J 3.8 Hz, J 6.9 Hz, J 7.9 Hz, 1H), 2.24 (m, 2H), 2.34 (br dd, J
11.0 Hz, 2H), 2.83 (m, 1H), 3.52 (br dd, J 11.0 Hz, 1H), 3.74 (m, J
4.1 Hz, J 2.5 Hz, 1H), 3.87 (m, 1H), 3.90 (m, 1H), 3.94 (m, 2H), 3.97
(m, 2H), 4.09 (dd, J 3.5 Hz, J 8.5 Hz, 1H), 4.65 (br dd, J 2.5 Hz, J
1
3
2
553–1557; (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2,
039–3042; (c) Plehiers, M.; Hootele, C. Can. J. Chem. 1996, 74, 2444–
453; (d) Angle, S. R.; Fevig, J. M.; Knight, S. D.; Marquis, R. W.;
1
3
Overman, L. E. J. Am. Chem. Soc. 1993, 115, 3966–3976; (e) Driessens,
F.; Hootele, C. Can. J. Chem. 1991, 69, 211–217.
. Yoshifuji, S.; Tanaka, K.; Kawai, T.; Nitta, Y. Chem. Pharm. Bull.
2.8 Hz, 1H); C NMR (125 MHz, D
61.1, 69.8, 73.8, 76.4; TOF MS ES+ calcd for C9H18NO3 : 188.1,
found 188.1; HRMS m/z calcd for C9H18NO3 : 188.1287, found
2
O): d 30.2, 35.4, 40.4, 54.2, 59.8,
þ
þ
5
6
1986, 34, 3873.
188.1264.
2
D
0
. For a comprehensive review on [2+2] cycloadditions, see: Tidwell, T.
T. Ketenes; John Wiley and Sons: Toronto, 1995. For other reviews,
see: (a) Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159–646; (b)
Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 1219; (c)
Ghosez, L.; Brynaert, J. M. In Comprehensive Organic Synthesis; Trost,
B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, pp 85–
9. Characterization data for 7 (HCl): Rf 0.20 (CHCl
3
/MeOH 1:1); ½aꢁ
ꢀ1
ꢀ8.75 (c 0.1, H
2
O); IR (film, cm ): 3310, 2952, 2889, 1597, 1455,
1
1368, 1339, 1115, 1083, 1049; H NMR (300 MHz, CDCl
3
): d 1.62–
1.77 (m, 2H), 1.85–2.20 (m, J 3.66 Hz, J 5.13 Hz, 4H), 2.61 (m, J
7.32 Hz, 1H), 3.17 (td, J 3.66 Hz, 13.18, 1H), 3.51 (br td, 1H), 3.58 (br
dd, J 1.41 Hz, 1H), 3.72–4.00 (m, J 2.93 Hz, 3H), 3.80 (t, J 2.20 Hz,
1
3
122; (d) Snider, B. B. ChemTracts-Org. Chem. 1991, 4, 403; (e) Tidwell,
1H), 4.30 (br s, 1 H); C NMR (75 MHz, CDCl
3
): d 13.8 (CH), 28, 2
), 59.8 (CH ), 62.6
T. T. Acc. Chem. Res. 1990, 23, 273; (f) Ghosez, L.; O’Donnell, M. J. In
Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic
Press: New York, 1977; pp 79–140.
(CH ), 28.6 (CH ), 40.8 (CH), 46.4 (CH ), 58.8 (CH
(CH), 63.1 (CH), 65.8 (CH); ESI-MS calcd for [M+H] : 202.2, found
202.2.
2
2
2
2
2
+