S. Elango et al. / Tetrahedron Letters 43 (2002) 3757–3759
3759
Hz, 1H, HCꢀCH), 4.41 (dd, J=7.6, 3.6 Hz, 1H, HC-
OH), 4.16–4.13 (m, 2H, O-CH-CH-O), 3.57 (t, J=4.0
Hz, 1H, HC-N), 2.24–2.15 (bs, 3H, OH, NH2), 1.40 (s,
3H, H3C-C-CH3), 1.33 (s, 3H, H3C-C-CH3).
6. (a) Tian, X.; Hudlicky, T.; Konigsberger, K. J. Am.
Chem. Soc. 1995, 117, 3643; (b) Hudlicky, T.; Tian, X.;
Konigsberger, K.; Maurya, R.; Rouden, J.; Fan, B. J.
Am. Chem. Soc. 1996, 118, 10752.
Scheme 4. A one-step conversion of 1 to 13.
1
7. Selected data for 8: H NMR (400 MHz, CDCl3) l 7.77
(d, J=6.8 Hz, 2H), 7.31 (d, J=6.8 Hz, 2H), 5.91 (ddd,
J=10.0, 4.4, 0.8 Hz, 1H), 5.72 (ddd, J=10.0, 2.0, 0.8 Hz,
1H), 4.50 (dd, J=6.4, 1.6 Hz, 1H), 4.36 (dt, J=6.8, 2.0
Hz, 1H), 3.34 (dd, J=6.4, 1.6 Hz, 1H), 3.23 (dd, J=6.4,
4.4 Hz, 1H), 2.41 (s, 3H), 1.33 (s, 3H), 1.31 (s, 3H).
8. (a) Knight, J. G.; Muldowney, M. P. Synlett 1995, 949;
(b) The Mitsunobu-type reactions used for the ring clo-
sure of the achiral hydroxy sulfonamide occurred in poor
yield (15% yield), see: Olivo, H. F.; Hemenway, M. S.;
Hartwig, A. C.; Chan, R. Synlett 1998, 247.
Acknowledgements
National Science Council of the Republic of China
provides generous support of this program (NSC 88-
2113-M-005-006).
References
9. Tf2O/2,6-di-t-butylpyridine-mediated intramolecular aryl-
ations within the piperonylated ethers have been reported
to give cyclic ether; see: Doyle, T. J.; Hendrix, M.;
VanDerveer, D.; Javanmard, S.; Haseltine, J. Tetrahedron
1997, 53, 11153.
1. (a) Hudlicky, T.; Olivo, H. F. Tetrahedron Lett. 1991, 32,
6077 and references cited therein; (b) Schurrle, K.; Beier,
B; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1 1991,
2407. For previous work on syntheses of conduramine,
see: (c) Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.;
Winkler, J. Liebigs Ann. Chem. 1987, 1129; (d) Braun, H.;
Burger, W.; Kresze, G.; Schmidtchen, F. P. Tetrahedron:
Asymmetry 1990, 1, 403 and earlier references therein; (e)
Werbitzky, O.; Klier, K.; Felber, H. Liebigs Ann. Chem.
1990, 267; (f) Johnson, C. R.; Ple, P. A.; Su, L.; Heeg, M.
J.; Adams, J. P. Synlett 1992, 388.
10. Selected data for 11b: 1H NMR (400 MHz, CDCl3) l
7.65 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H), 6.51 (s,
1H), 6.39 (s, 1H), 6.05 (dd, J=10.0, 5.2 Hz, 1H), 5.92
(dd, J=9.6, 3.6 Hz, 1H), 5.85 (s, 2H), 4.63 (d, J=16.8
Hz, 1H), 4.54 (dd, J=4.4, 4.0 Hz, 1H), 4.27 (d, J=16.8
Hz, 1H), 4.26–4.21 (m, 2H), 3.48 (dd, J=4.8, 4.4 Hz,
1H), 2.34 (s, 2H), 1.45 (s, 3H), 1.33 (s, 3H); 13C NMR
(75.5 MHz, CDCl3) l 146.88, 146.20, 143.20, 136.78,
131.33, 129.33, 128.59, 127.55, 125.67, 124.85, 109.51,
107.37, 106.11, 100.96, 72.31, 71.55, 53.81, 44.02, 36.46,
27.89, 26.13, 21.41; [h]2D5 −101.7 (c 1.7, CH2Cl2).
2. (a) Hudlicky, T.; Olivo, H. F. J. Am. Chem. Soc. 1992,
114, 9694; (b) Hudlicky, T.; Olivo, H. F.; McKibben, B.
J. Am. Chem. Soc. 1994, 116, 5108; (c) McIntosh, M. C.;
Weinreb, S. M. J. Org. Chem. 1993, 58, 4823.
3. Sutbeyaz, Y.; Secen, H.; Balci, M. J. Chem. Soc., Perkin
11. Trost, B. M.; Pulley, S. R. J. Am. Chem. Soc. 1995, 117,
10143 and references cited therein.
Trans. 1 1988, 1330.
4. (a) Yan, T.-H.; Tan, C.-W.; Lee, H.-C.; Lo, H.-C.;
Huang, T.-Y. J. Am. Chem. Soc. 1993, 115, 2613; (b) Lin,
C.-C.; Wang, Y.-C.; Hsu, J.-L.; Chiang, C.-C.; Su, D.-
W.; Yan, T.-H. J. Org. Chem. 1997, 62, 3806; (c) Exten-
sive studies have revealed that camphor-based
chloronitroso 6a has shown exceptionally high stereose-
lection in cycloadditions; additional details will be pub-
lished elsewhere.
1
12. Selected data for 13: H NMR (400 MHz, CDCl3) l 5.85
(dt, J=10.0, 2.8 Hz, 1H), 5.73 (dt, J=10.0, 2.8 Hz, 1H),
5.13 (m, 1H), 4.30 (dd, J=8.0, 4.8 Hz, 1H), 4.14 (dd,
J=7.6, 6.0 Hz, 1H), 3.97 (m, 1H), 3.81 (s, 3H), 1.49 (s,
3H), 1.36 (s, 3H); 13C NMR (75.5 MHz, CDCl3) l
154.88, 128.61, 127.33, 109.93, 76.59, 76.11, 75.32, 60.63,
55.02, 27.01, 24.72, [h]2D5 −33.8 (c 0.9, CH2Cl2) [lit.11. [h]2D5
−34.0 (c 2.1, CH2Cl2)]; high-resolution MS (FAB+) m/e
Calcd for C11H16N3O5: 270.1089. Found: 270.1093.
1
5. Selected data for 1: H NMR (400 MHz, CDCl3) l 6.15
(dd, J=9.6, 4.4 Hz, 1H, HCꢀCH), 5.94 (dd, J=9.6, 4.4