The methoxycarbonylcarbene insertion into 1,3-dithiolane and 1,3-oxathiolane rings

Tetrahedron

Volumn 62, Issue 15, 2006, Pages 3610-3618

  Stepakov, Alexander V ^a   Molchanov, Alexander P ^a   Magull, Jörg ^b   Vidović, Denis ^b   Starova, Galina L ^a   Kopf, Jürgen ^c   Kostikov, Rafael R ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Carbenes; Diazocompounds; Dithiolanes; Oxathiolanes; Ring expansion; Sigmatropic rearrangement; Stevens rearrangement; Ylides

Indexed keywords

1,3 DITHIOLANE DERIVATIVE; 1,3 OXATHIOLANE DERIVATIVE; ACETOACETIC ACID; CARBENOID; CARBOXYLIC ACID DERIVATIVE; HALIDE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; PRIORITY JOURNAL; REACTION ANALYSIS; STEVENS REARRANGEMENT; SUBSTITUTION REACTION;

EID: 33645007610     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.100     Document Type: Article

References (37)

1. Y. Kawamura, K. Akitomo, M. Oe, T. Horie, and M. Tsukayama Tetrahedron Lett. 38 1997 8989 8992
2. V.K. Aggarwal, P. Blackburn, R. Fieldhouse, and R.V.H. Jones Tetrahedron Lett. 39 1998 8517 8520
3. M. Hamaguchi, T. Misumi, and T. Oshima Tetrahedron Lett. 39 1998 7113 7116
4. R. Imashiro, T. Yamanaka, and M. Seki Tetrahedron: Asymmetry 10 1999 2845 2851
5. M. Catasús, A. Moyano, and V.K. Aggarwal Tetrahedron Lett. 43 2002 3475 3479
6. Y.N. Romashin, M.T.H. Liu, B.T. Hill, and M.S. Platz Tetrahedron Lett. 44 2003 6519 6521
7. A.V. Novikov, A. Sabahi, A.M. Nyong, and J.D. Rainier Tetrahedron: Asymmetry 14 2003 911 915
8. X. Zhang, M. Ma, and J. Wang Tetrahedron: Asymmetry 14 2003 891 895
9. Y. Sawada, and A. Oku J. Org. Chem. 69 2004 2899 2901
10. S. Zhu, S. Zhu, and Y. Liao J. Fluorine Chem. 125 2004 1071 1076
11. M.P. Doyle, D.G. Ene, D.C. Forbes, and J.S. Tedrow Tetrahedron Lett. 38 1997 4367 4370
12. D.M. Hodgson, and M. Petroliagi Tetrahedron: Asymmetry 12 2001 877 881
13. S. Kitagaki, Y. Yanamoto, H. Tsutsui, M. Anada, M. Nakajima, and S. Hashimoto Tetrahedron Lett. 42 2001 6361 6364
14. S.N. Osipov, N. Sewald, A.F. Kolomiets, A.V. Fokin, and K. Burger Tetrahedron Lett. 37 1996 615 618
15. K.W. Glaeske, B.N. Naidu, and F.G. West Tetrahedron: Asymmetry 14 2003 917 920
16. G.J. Rowlands, and W.K. Barnes Tetrahedron Lett. 45 2004 5347 5350
17. M.P. Doyle Chem. Rev. 86 1986 919 939
18. A. Padwa, and S.F. Hornbruckle Chem. Rev. 91 1991 263 309
19. A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223 269
20. M.P. Doyle Chem. Rev. 98 1998 911 935
21. V.K. Aggarwal, M. Ferrara, R. Hainz, and S.E. Spey Tetrahedron Lett. 40 1999 8923 8927
22. S. Kitagaki, Y. Yanamoto, H. Okubo, M. Nakajima, and S. Hashimoto Heterocycles 54 2000 623 628
23. R.J. Ponsford Tetrahedron Lett. 21 1980 2451 2452
24. S. Sengupta, and S. Mondal Tetrahedron Lett. 41 2000 2965 2969
25. C.D. Gutsche, and M. Hillman J. Am. Chem. Soc. 76 1954 2236 2240
26. A.P. Molchanov, T.G. Serkina, L.A. Badovskaya, and R.R. Kostikov Zh. Org. Khim. 28 1992 2320 2324 Russian J. Org. Chem. 1992, 28, 1874-1877
27. A.P. Molchanov, A.V. Stepakov, J. Kopf, I.G. Zenkevich, and R.R. Kostikov Russ. Chem. Bull. Int. Ed. 50 2001 2144 2148 Izv. Acad. Nauk. Ser. Khim. 2001, 2048-2052
28. M.P. Doyle, J.H. Griffin, M.S. Chinn, and D. van Leusen J. Org. Chem. 49 1984 1917 1925
29. M. Ioannou, M.J. Porter, and F. Saez Tetrahedron 61 2005 43 50
30. E. Vedeis, and J.P. Hagen J. Am. Chem. Soc. 97 1975 6878 6880
31. (a) Golodnikov, G. V.; Mandel'shtam, T. V. Praktikum Organich. Sintezu (Laboratory Mannual Org. Synth.), LGU: Leningrad, 1976, 219-223.
32. (b) Org. Synth. 1956, 36, 25-28.
33. J.R. Williams, and G.M. Sarkisian Synthesis 1974 32 33
34. L.L. Yeung, Y.C. Yip, and T.-Y. Luh J. Org. Chem. 55 1990 1874 1881
35. Z.-J. Ni, and T.-Y. Luh Org. Synth. 70 1992 240 245
36. G.E. Wilson, M.G. Huang, and W.W. Schloman J. Org. Chem. 33 1968 2133 2134
37. B. Karimi, and H. Seradj Synlett 2000 805 806