T. L. S. Kishbaugh, G. W. Gribble / Tetrahedron Letters 42 (2001) 4783–4785
4785
References
119.8, 115.7, 113.9, 102.5. Compound 8: mp 172–172.5°C;
IR (film) wmax 3328 (OH), 1702 (CꢀO) cm−1; (EtOH) umax
1
1. (a) For an excellent review, see: Lee, L.; Snyder, J. K.
Adv. Cycloaddit. 1999, 6, 119–171; (b) For a recent
example, see: Hsieh, M.-F.; Rao, P. D.; Liao, C.-C.
Chem. Commun. 1999, 1441–1442.
2. Benson, S. C.; Lee, L.; Yang, L.; Snyder, J. K. Tetra-
hedron 2000, 56, 1165–1180 and previous papers.
3. Raasch, M. S. J. Org. Chem. 1980, 45, 856–867.
4. Wenkert, E.; Moeller, P. D. R.; Piettre, S. R. J. Am.
Chem. Soc. 1988, 110, 7188–7194.
230, 264, 294, 330 nm. H (CD3COCD3): l 8.74 (s, 1H),
8.26 (d, 1H, 8 Hz), 7.88–7.96 (m, 3H), 7.29–7.40 (m, 2H),
6.94 (d, 1H, 8 Hz), 4.58 (q, 2H, 7 Hz), 1.53 (t, 3H, 7 Hz);
13C (CD3COCD3): l 158.6, 153.1, 140.7, 139.0, 127.1,
126.4, 124.2, 121.4, 119.6, 119.2, 116.9, 112.9, 103.9, 63.9,
14.8; Anal. calcd for C15H13NO3: C, 70.58; H, 5.13; N,
5.49. Found: C, 70.20; H, 5.13; N; 5.41. Compound 10:
mp 197–198°C; IR (film) wmax 3401 (OH), 1723 (CꢀO)
;
cm−1 (EtOH) umax 232, 274, 296, 304 nm. 1H
5. (a) Kraus, G. A.; Raggon, J.; Thomas, P. J.; Bougie, D.
Tetrahedron Lett. 1988, 29, 5605–5608; (b) Kraus, G. A.;
Bougie, D.; Jacobson, R. A.; Su, Y. J. Org. Chem. 1989,
54, 2425–2428.
6. (a) Gieseler, A.; Steckhan, E.; Wiest, O. Synlett 1990,
275–277; (b) Gieseler, A.; Steckhan, E.; Wiest, O.;
Knoch, F. J. Org. Chem. 1991, 56, 1405–1411; (c) Wiest,
O.; Steckhan, E.; Grein, F. J. Org. Chem. 1992, 57,
4034–4037; (d) Wiest, O.; Steckhan, E. Tetrahedron Lett.
1993, 34, 6391–6394.
(CD3COCD3): l 8.42 (s, 1H), 8.30 (d, 1H, 8 Hz), 8.15 (d,
1H, 9 Hz), 8.01 (m, 1H), 7.44–7.52 (m, 2H), 7.32–7.37 (m,
1H), 7.03 (dd, 1H, 2.5, 9 Hz), 4.58 (q, 2H, 7 Hz), 1.53 (t,
3H, 7 Hz). 13C (CD3COCD3): l 154.9, 152.9, 139.7,
132.9, 128.1, 127.8, 126.7, 123.9, 120.7, 117.9, 117.1,
116.5, 106.1, 63.8, 14.8. Anal. calcd for C15H13NO3: C,
70.58; H, 5.13; N, 5.49. Found: C, 70.19; H, 5.20; N,
1
5.38. Compound 12: H (CDCl3): l 8.32 (d, 1H, 8 Hz),
8.20 (d, 1H, 9 Hz), 7.93 (d, 1H, 7 Hz), 7.45–7.52 (m, 2H),
7.34–7.39 (m, 1H), 7.03 (dd, 1H, 2, 9 Hz), 4.60 (q, 2H, 7
Hz), 1.57 (t, 3H, 7.32 Hz), 1.10 (t, 9H, 3 Hz), 0.31 (t, 6H,
3 Hz); 13C (CDCl3): l 152.6, 152.2, 139.1, 133.4, 127.5,
127.3, 126.1, 123.3, 120.2, 119.9, 117.2, 116.6, 110.5, 63.2,
30.0, 26.1, 26.0, 18.6, 14.8, −2.6, −4.1; MS m/z 404
([M+Cl]), 370 (MH+), HRMS m/z calcd for C21H27NO3Si
(M+) 369.1760, found 369.1763. Compound 14: 1H
(CDCl3): l 8.34 (d, 1H, 8 Hz), 8.21 (d, 1H, 9 Hz), 7.86 (d,
1H, 7 Hz), 7.78–7.82 (m, 2H), 7.30–7.54 (m, 6H), 7.03
(dd, 1H, 2, 9 Hz), 1.06 (s, 9H), 0.27 (s, 6H). 13C (CDCl3):
l 152.9, 139.2, 137.9, 133.9, 133.3, 129.1, 127.9, 127.7,
126.8, 126.7, 124.1, 120.4, 120.3, 116.3, 115.7, 110.6, 25.9,
18.4, −2.7, −4.2.
7. Markgraf, J. H.; Patterson, D. E. J. Heterocyclic Chem.
1996, 33, 109–111.
8. Padwa, A.; Brodney, M. A.; Dimitroff, M. J. Org. Chem.
1998, 63, 5304–5305.
9. Biolatto, B.; Kneeteman, M.; Mancini, P. Tetrahedron
Lett. 1999, 40, 3343–3346.
10. (a) Pelkey, E. T.; Gribble, G. W. Chem. Commun. 1997,
1873–1874; (b) Gribble, G. W.; Pelkey, E. T.; Switzer, F.
L. Synlett 1998, 1061–1062; (c) Gribble, G. W.; Pelkey, E.
T.; Simon, W. M.; Trujillo, H. A. Tetrahedron 2000, 56,
10133–10140.
11. (a) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62,
5252–5253; (b) Huang, Y.; Iwama, T.; Rawal, V. H. J.
Am. Chem. Soc. 2000, 122, 7843–7844 and previous
papers.
14. Kishbaugh, T. L. S.; Jasinski, J.; Gribble, G. W., unpub-
lished results.
15. (a) Cummins, J. A.; Tomlinson, M. L. J. Chem. Soc.
1955, 3475–3477; (b) Compound 9: mp 262–263°C; lit.
mp 262–264°C: Benzies, D. W. M.; Fresneda, P. M.;
Jones, R. A.; McNab, H. J. Chem. Soc., Perkin Trans 1
1986, 1651–1654; (c) This is also commercially available.
16. Pelkey, E. T.; Gribble, G. W. Tetrahedron Lett. 1997, 38,
5603–5606.
17. (a) Ruff, O.; Stein, V. Ber. 1901, 34, 1668–1684; (b)
Compound 11: mp 257–258°C; lit. mp 259–260°C: Bis-
agni, E.; Ducrocq, C.; Hung, N. C. Tetrahedron 1980, 36,
1327–1330.
18. Wiley, R. H.; Jarboe, C. H. J. Am. Chem. Soc. 1956, 78,
2398–2401.
19. Corey, E. J.; Kozikowski, A. P. Tetrahedron Lett. 1975,
2389–2392.
20. Kraus, G. A.; Zhang, N.; Melekhov, A.; Jensen, J. H.
Synlett 2001, 521–522.
12. Pelkey, E. G.; Gribble, G. W. Synthesis 1999, 1117–1122.
13. Compound 6: mp 178–179°C; IR (film) wmax 1722 (CꢀO),
1361 (SO2), 1166 (SO2) cm−1; (EtOH) umax 256 nm. 1H
(CD2Cl2): l 7.73–7.80 (m, 3H), 7.55–7.62 (m, 2H), 7.42–
7.52 (m, 3H), 7.15–7.20 (m, 1H), 5.70 (dd, 1H, 2, 6 Hz),
4.67 (m, 1H), 3.46 (s, 3H), 3.20 (dd, 1H, 6, 16 Hz), 3.15
(dd, 1H, 2, 16 Hz), 2.67 (dd, 1H, 3, 19 Hz), 1.92 (dd, 1H,
3, 19 Hz). 13C (CD2Cl2): l 204.2, 142.7, 136.2, 134.4,
133.5, 129.6, 127.9, 125.9, 125.6, 125.4, 116.8, 96.1, 20.5,
62.0, 58.3, 44.5, 37.7; Anal. calcd for C19H18N2O6S: C,
56.71; H, 4.51; N, 6.96; S, 7.97. Found: C, 56.40; H, 4.45;
N, 6.88; S, 7.91. Compound 7: IR (film) wmax 3347 (OH),
1367 (SO2), 1176 (SO2) cm−1; UV (EtOH) umax 224, 260
nm; 1H (CD3COCD3): l 8.84 (s, 1H), 8.27 (d, 1H, 7.5
Hz), 7.84–7.91 (m, 5H), 7.34–7.59 (m, 5H), 6.95 (dd, 1H,
2, 8 Hz); 13C (CD3COCD3): l 158.7, 140.7, 139.0, 138.6,
135.2, 130.3, 127.8, 127.3, 126.8, 125.2, 122.0, 120.2,
.