4784
K. C. Majumdar et al. / Tetrahedron Letters 50 (2009) 4781–4784
11. Doye, S.; Hotopp, T.; Winterfeldt, E. J. Chem. Soc., Chem. Commun. 1997, 1491.
Me
12. Mustafa, A.; Hilmy, M. K. J. Chem. Soc. 1952, 1339.
O
O
13. Shearing, E. A.; Smiles, S. S. J. Chem. Soc. 1937, 1348.
S
Me
14. Truce, W. E.; Hoerger, F. D. J. Am. Chem. Soc. 1954, 76, 5357.
15. Deacon, T.; Farrar, C. R.; Sikkel, J.; Williams, A. J. Am. Chem. Soc. 1978, 100, 2525.
16. Hanson, G.; Kemp, D. S. J. Org. Chem. 1981, 46, 5441.
17. Schetty, G. Helv. Chim. Acta 1949, 32, 24.
18. Schetty, G. Helv. Chim. Acta 1947, 30, 1650.
O
[Pd0]
O
O
Br
S
10a
O
HBr
19. Drozd, V. N.; Saks, T. K. Zh. Org. Khim. 1975, 11, 351.
20. Bovenschult, E.; Metz, P.; Henkel, G. Angew. Chem. 1989, 101, 204. Angew.
Chem., Int. Ed. Engl. 1989, 28, 202.
21. (a) Metz, P.; Fleischer, M. Synlett 1993, 399; (b) Metz, P.; Fleischer, M.; Fröhlich,
R. Tetrahedron 1995, 51, 711.
3a
Me
Me
BrPd
22. Plietker, B.; Seng, D.; Fröhlich, R.; Metz, P. Tetrahedron 2000, 56, 873.
23. Wolckenhauer, S. A.; Devlin, A. S.; Bois, J. D. Org. Lett. 2007, 9, 4363.
24. (a) Karsch, S.; Schwab, P.; Metz, P. Synlett 2002, 2015; (b) Flohic, A. L.; Meyer,
C.; Cossy, J.; Desmurs, J.-R.; Galland, J.-C. Synlett 2003, 667.
25. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
26. Flohic, A. L.; Meyer, C. J. C. Org. Lett. 2005, 7, 339.
O
O
O
S
PdBr S
O
O
O
27. Flohic, A. L.; Meyer, C. J. C. Tetrahedron 2006, 62, 9017.
28. Tamaru, Y.; Nagao, K. J. Org. Chem. 1990, 55, 1823.
12
11
Scheme 3. Plausible mechanism.
29. Majumdar, K. C.; Mondal, S.; De, N. Synlett 2008, 2851.
30. (a) Majumdar, K. C.; Mondal, S. Tetrahedron Lett. 2007, 48, 6951; (b) Majumdar,
K. C.; Mondal, S. Tetrahedron Lett. 2008, 49, 2418; (c) Majumdar, K. C.;
Chattopadhyay, B.; Ray, K. Tetrahedron Lett. 2007, 48, 7633; (d) Majumdar, K.
C.; Chattopadhyay, B.; Nath, S. Tetrahedron Lett. 2008, 49, 1609; (e) Majumdar,
K. C.; Chakravorty, S.; De, N. Tetrahedron Lett. 2008, 49, 3419.
31. Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
Acknowledgments
32. Compound 3a: white solid, mp 108–110 °C, yield 94%. IR (KBr, cmÀ1
) mmax:
We thank DST (New Delhi) and CSIR (New Delhi) for financial
assistance. One of us S.M. is thankful to DST (New Delhi) and
D.G. is grateful to CSIR (New Delhi) for fellowships.
2923, 1351; 1H NMR (CDCl3, 400 MHz) d: 2.44 (s, 3H), 7.30 (d, 2H, J = 8.2 Hz),
7.47 (d, 1H, J = 9.2 Hz), 7.52 (t, 1H, J = 7.2 Hz), 7.59 (t, 1H, J = 7.2 Hz), 7.79 (d,
2H, J = 8.3 Hz), 7.83 (d, 2H, J = 7.0 Hz), 8.18 (d, 1H, J = 8.5 Hz); 13C NMR (CDCl3,
100 MHz) d: 21.8, 116.1, 121.7, 126.9, 127.5, 128.0, 128.1, 128.2, 128.7, 129.0,
129.9, 130.1, 132.6, 132.9, 145.1, 145.8; HRMS: calcd for C17H13BrO3S:
398.9667 [M+Na], 400.9540 [M+2+Na]. Found: 398.9666 [M+Na], 400.9666
[M+2+Na].
References and notes
1. Schultz, G. Chem. Ber. 1887, 20, 3158.
2. Eedmann, H. Ann. Chem. 1888, 247, 306.
3. Roberts, D. W.; Williams, D. L. Tetrahedron 1987, 43, 1027.
4. Roberts, D. W. Org. Process Res. Dev. 1998, 2, 194.
5. Meschkat, E.; Barratt, M. D.; Lepoittevin, J.-P. Chem. Res. Toxicol. 2001, 14, 110–
118.
33. General procedure for the synthesis of sultones 10(a–g) by the Pd-catalyzed
cyclization
reaction:
A
mixture
of
3a
(300 mg,
0.79 mmol),
tetrabutylammonium bromide (308 mg, 0.96 mmol), and dry potassium
acetate (214 mg, 2.19 mmol) was taken in dry N,N- dimethylformamide
(6 mL) under nitrogen atmosphere. Pd(PPh3)4 (17.8 mg, 0.079 mmol) was
added and the reaction mixture was stirred at 100 °C for 1 h. The reaction
mixture was cooled and water (25 mL) was added. The aqueous layer was
extracted with ethyl acetate (3 Â 20 mL) and the organic layer was washed
with water (2 Â 25 mL), followed by brine (25 mL). The organic layer was dried
(Na2SO4), and the solvent was removed in vacuo. The crude product was
purified by silica gel column chromatography using ethyl acetate: petroleum
ether (1:9) to afford the product 10a. The other substrate 3(b–g) was similarly
treated to give products 10(b–g).
6. Pérez-Pérez, M.-J.; Balzarini, J.; Hosoya, M.; Clercq, E. D.; Camarasa, M. J. Bioorg.
Med. Chem. Lett. 1992, 2, 647.
7. For reviews on sultone chemistry see: (a) Mustafa, A. Chem. Rev. 1954, 57, 195;
(b) Fischer, R. F. Ind. Eng. Chem. 1964, 56, 41; (c) Buglass, A. J.; Tillet, J. G. In The
Chemistry of Sulfonic Acids, Esters and their Derivatives; Patai, S., Rappoport, Z.,
Eds.; John Wiley & Sons: New York, 1991; p 789. Chapter 19; (d) Metz, P. J.
Prakt. Chem. 1998, 340, 1.
8. Solas, D.; Wolinsky, J. J. Org. Chem. 1983, 48, 1988.
9. Metz, P.; Stölting, J.; Läge, M.; Krebs, B. Angew. Chem. 1994, 106, 2275. Angew.
Chem., Int. Ed. Engl. 1994, 33, 2195.
10. (a) Bernsmann, H.; Hungerhoff, B.; Fechner, R.; Fröhlich, R.; Metz, P.
Tetrahedron Lett. 2000, 41, 1721; (b) Bernsmann, H.; Fröhlich, R.; Metz, P.
Tetrahedron Lett. 2000, 41, 4347; (c) Bernsmann, H.; Gruner, M.; Metz, P.
Tetrahedron Lett. 2000, 41, 7629; (d) Wang, Y.; Bernsmann, H.; Gruner, M.;
Metz, P. Tetrahedron Lett. 2001, 42, 7801.
Compound 10a: White solid, mp 196–198 °C, yield 85%. IR (KBr, cmÀ1
) mmax:
1382, 1192; 1H NMR (CDCl3, 400 MHz) d: 2.55 (s, 3H), 7.42 (dd, 2H, J = 8.9,
2.8 Hz), 7.56 (t, 1H, J = 7.4), 7.65 (t, 1H, J = 7.3), 7.92 (dd, 2H, J = 9.2, 2.2 Hz),
7.97 (d, 1H, J = 7.9 Hz), 8.04 (s, 1H), 8.54 (d, 1H, J = 8.6 Hz); 13C NMR (CDCl3,
75 MHz) d: 22.1, 117.6, 118.3, 124.5, 125.1, 126.1, 128.1, 129.2, 129.3, 129.6,
129.7, 130.6, 131.5, 132.0, 132.5, 144.0, 147.9; HRMS: Calcd for C17H12O3S:
319.0405 [M+Na]. Found: 319.0405 [M+Na].