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M. J. Uddin et al.
PAPER
Table 7 Spectroscopic Data of the Cycloadducts 8a-c
Producta IR (KBr/Neat) 1H NMR (500 MHz, CDCl3/TMS)
13C NMR (125.76 MHz, CDCl3/TMS) HRMS (FAB), m/z, (M + 1)
n (cm-1)
d, J (Hz)
d
calcd
found
(S,S)-8a
3075, 2950
2925, 2850,
2800, 1660,
1580, 1500,
1450, 1300,
1140, 1080,
740, 680
1.24 (t, 1 H, J = 8.00), 3.10 (d, 2 H, J = 38.60 (CH2), 57.10 (CH2), 58.40 (CH2), 433.1585
12.00), 3.45 (d, 2 H, J = 12.00), 3.80 (d, 61.40 (CH), 77.40 (CH2) 84.90 (C-
1 H, J = 12.00), 4.11 (d, 1 H, J = 8.00), SO2), 128.50-137.50 (Ph), 150.50
4.87 (d, 1 H, J = 8.00), 7.52-6.81 (m, (PhSO2), 164.90 (C=N)
15 H)
433.1561
(S,S)-8b
(S,S)-8c
3090, 3070
3050, 2950,
2925, 2850,
2800, 1680,
1550, 1300
740, 680
1.14 (d, 3 H, J = 6.03), 2.27 (d, 1 H, J = 17.09 (CH3), 53.43 (CH2), 56.47 (CH2), 357.1272
11.24), 2.85 (d, 1 H, J = 13.40), 3.41 (d, 76.79 (CH), 77.25(CH2) 80.90 (C-
1 H, J = 11.48), 3.76 (d, 1 H, J = 13.19), SO2),137.71-127.10 (Ph),143.89
3.96 (d, 1 H, J = 9.00), 3.98-4.00 (m, (PhSO2), 163.08
1 H) 4.26 (d, 1 H, J = 8.99), 7.76-6.87
357.1309
385.1576
(m, 10 H) (C=N)
3075, 2990
2980, 2950,
2925, 2850,
1660, 1600,
1210, 1140,
1030, 750
1.08 (d, 3 H, J = 6.85), 1.17 (d, 3 H, J = 216.19 (CH3),18.54 (CH3), 29.25 (CH), 385.1585
6.90), 2.14-2.19 (m, 1 H), 3.20 (d, 1 H, 53.99 (CH2), 58.93 (CH2), 64.34
J = 12.80), 3.52 (d, 1 H, J = 12.85),
3.92-3.96 (m, 1 H), 4.06 (d, 1 H, J = 137.54-127.01 (Ph), 150.32 (PhSO2),
9.90), 4.10 (s, 2 H), 4.72 (d, 1 H, J =
10.12), 7.89-7.17 (m, 10 H)
(CH),76.34(CH2),85.09 (C-SO2),
164.53 (C=N)
a All compounds are colored syrups.
b 400 MHz NMR spectrum.
tion (0.5 mL) followed by H2O (0.5 mL). The mixture was then re-
fluxed again for 15 min and the solids that appeared were filtered
after cooling. After drying (MgSO4), the solvent was removed and
the resultant mass was chromatographed on silica gel (CH2Cl2) and
the product obtained was recrystallized from isopropyl alcohol to
afford the isoxazolidine derivative (S,R,S)-10a as white crystals
(88%); mp 112-113°C.
(2) Hassner, A.; Maurya, R.; Friedman, O; Gottlieb, H.E. J. Org.
Chem. 1993, 58, 4539.
For general reviews on 1,3-dipolar cycloaddition, see:
Kozikowski, A.P. Acc. Chem. Res. 1984, 32, 1.
Kanemasa, S; Tsuge, O. Heterocycles 1990, 30, 719.
Carruthers, W. Cycloaddition Reactions in Organic
Synthesis, Pergamon: Oxford, 1990, p 285.
Wade, P.A. Comprehensive Organic Synthesis, Trost, B.M.,
Ed.; Pergamon: Oxford, 1991,, Vol. 4; p 1111.
Little, R.D. Comprehensive Organic Synthesis, Trost, B.M.,
Ed.; Pergamon: Oxford, 1991, Vol. 5; p 239.
(3) (a) Padwa, A. Angew. Chem., Int. Ed. Engl. 1976, 15, 123.
(b) Padwa, A.; Schoffstall, A.M. Adv. Cycloadd. 1990; 2, 1.
(c) Rai, K.M.L., Hassner, A. Heterocycles 1990, 30, 817.
(4) (a) Oppolzer, W.; Angew. Chem.,Int. Ed. Engl. 1977,16, 10.
(b) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1.
(c) Terao, Y.; Aono, M.; Achiwa, K. Heterocycles 1988, 27,
981.
HRMS (FAB): m/z (M + 1) calcd for C25H27N2O: 371.2123, found:
371.2122.
IR(KBr): n = 3020 (CH, C6H5), 2950 (aliphatic CH), 1592 (C=C,
C6H5),1488 (Ph), 1460 (Ph), 1082 (C-N), 1080, 750, 690 cm-1.
1H NMR (500MHz, CDCl3/TMS): d = 2.16-2.14 (m, 1 H), 2.93-
2.90 (m, 1 H),3.01 (d, 1 H, J = 5.65 Hz), 3.23-3.11 (m, 3), 3.28 (dd,
1 H, J = 14.6, 14.6 Hz), 3.71 (m, 2 H), 4.05 (m, 1 H), 4.15 (d, 1 H,
J = 13.0 Hz), 7.43-6.68 (m, 15 H).
13C NMR (125.76MHz, DEPT, CDCl3): d = 37.45 (CH2), 46.13
(CH), 57.97 (CH), 58.94 (CH2), 70.03 (CH), 71.08 (CH2), 75.61
(CH), 129.92-114.41 (Ph), 138.61 (PhN), 150.73 (PhSO2).
(5) De Shong, P.; Leginus, J. M.; Lander, S. W. J. Org. Chem.
1986, 51, 574.
(6) Kametani, T.; Chu, S.-D. T. J. Chem. Soc. Perkin. Trans. 1
1988, 1598.
(7) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L.;
Tetrahedron 1987, 43, 4051
Crystal Data for 3a and 3e
See Tables 8 and 9, respectively.
(8) (a) Tufariello, J. J. Acc. Chem. Res. 1979, 11, 369.
(b) Ali, S. A.; Khan, J. H.; Wazeer, M. I. M. Tetrahedron
1988, 44, 5911.
Acknowledgement
We wish to thank Mr. Kouichi Mizuki of Yoshitomi Pharmaceutical
Co., Ltd., for the HRMS measurements. This work was supported
by Grant-in Aid for COE Research (10CE 2003) by the Ministry of
Education, Science, Sports and Culture of Japan.
(c) Hall, A.; Meldrum, K. P.; Therond, P.R.; Wightman, R. H.
Synlett 1997, 123.
(d) Goti, A.; Fedi, V.; Nanneli, L.; De Sarlo, F.; Brandi, A.
Synlett 1997, 577.
(9) Moriyama, S.; Vallée, Y. Synthesis 1998, 4, 393.
(10) (a) Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry,
Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol 2.
(b) Tufariello, J. Acc. Chem. Res. 1979, 12, 396.
References
(1) Rossiter, B.F.; Swingle, N. M. Chem.Rev. 1992, 92, 771.
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