Novel synthesis of 5,6-dihydro-4H-thieno[3,2-b]pyrrol-5-ones via the rhodium(II)-mediated Wolff rearrangement of 3-(thieno-2-yl)-3-oxo-2-diazopropanoates

Organic Letters

Volumn 4, Issue 6, 2002, Pages 873-876

  Lee, Dong Joon ^a   Kim, Kyongtae ^a   Park, Yung Ja ^b  

^a Seoul National University   (South Korea)

^b Sookmyung Women's University   (South Korea)

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ARTICLE;

EID: 0001142459     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016995n     Document Type: Article

References (21)

1. Baker, A. J.; Kettle, J. G.; Faull, A. W. PCT Int. Appl. WO 9940, 914, GB Appl. 1998/ 3, 228; Chem. Abstr. 1999, 131, 170342d.
2. Blair, J. B.; Marona-Lewicka, D.; Kanthasamy, A.; Lucaites, V. L.; Nelson, D. L.; Nichols, D. E. J. Med. Chem. 1999, 42, 1106.
3. (a) Soth, S.; Farnier, M.; Paulmier, C. Can. J. Chem. 1978, 56, 1429.
4. (b) Mamaev, V. P.; Lyubimova, E. N. Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 1607.
5. Gale, W. W.; Scott, A. N.; Snyder, H. R. J. Org. Chem. 1964, 29, 2160.
6. (a) Srinivasan, K.; Srinivasan, K. G.; Balasubramanian, K. K.; Swaminathan, S. Synthesis 1973, 313.
7. (b) Chippendale, K. E.; Iddon, B.; Suschitzky, H. J. Chem. Soc., Chem. Commun. 1971, 203.
8. (a) Soth, S.; Farnier, M.; Paulmier, C. Can. J. Chem. 1978, 56, 1710.
9. (b) Hemetsberger, H.; Knittel, D. Monatsh. Chem. 1972, 103, 194.
10. Gairns, R. S.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1985, 1818.
11. (a) Shvedov, V. I.; Vasiléva, V. K.; Khanzomenova, I. A.; Grinev, A. N. Khim. Geterotsikl. Soedin, 1975, 767.
12. (b) Shevedov, V. I.; Vasiléva, V. K.; Kharizomenova, I. A.; Otkrytiya, A. N. Grinev. Izobret., Prom. Obraztsy, Tovarnye Znaki 1973, 50, 62.
13. Wensbo, D.; Annby, U.; Gronowitz, S. Tetrahedron 1995, 51, 10323.
14. Kim, B.; Kim, K. J. Org. Chem. 2000, 65, 3690.
15. (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
16. (b) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
17. (c) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
18. (d) Ueda, Y.; Roberge, G.; Vinet, V. Can. J. Chem. 1984, 62, 2936.
19. 1 = Bn (entries 5 and 6), the absorptions of the benzylic protons of 18 and 19 are 4.82-4.95 and 5.15 ppm, respectively.
20. Harrison, J. F. In Carbene Chemistry, 2nd ed.; Kirmse, W.; Academic Press: New York, 1971; Chapter 12, pp 457-503.
21. Nonhebel, D. C.; Walton, J. C. Free-Radical Chemistry, Cambridge University Press: New York, 1974; Chapter 10, pp 305-416.