Cyclopropane ring formation by an SmI2 mediated cyclisation of δ-halo-α,β-unsaturated esters

Tetrahedron Letters

Volumn 40, Issue 49, 1999, Pages 8557-8561

  David, Hervé ^a   Afonso, Carlos ^a   Bonin, Martine ^a   Doisneau, Gilles ^a   Guillerez, Marie George ^a   Guibé, François ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Cyclisations; Cyclopropanes; Radical reactions; Samarium; Samarium compounds

Indexed keywords

CYCLOPROPANE; ESTER; PROTON; RADICAL; SAMARIUM;

ARTICLE; CYCLIZATION;

EID: 0033521160     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01816-X     Document Type: Article

References (32)

1. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.
2. Reviews: (a) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354;
3. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
4. Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429.
5. 2 mediated stereoselective 4-exo-trig cyclisation of unsaturated aldehydes to cyclobutanols was reported by Procter and co-workers (Johnston, D.; McCuster, C. M.; Procter, D. J. Tetrahedron Lett. 1999, 40, 4913-4916).
6. Barton, D. H. R.; Basu, N. K.; Hesse, R. H.; Morehouse, F. S.; Pechet, M. J. M. J. Am. Chem. Soc. 1966, 88, 3016-3021. We are very grateful to the referee for informing us of this early work.
7. 2 could thus be determined.
8. Nonhebel, D. C. Chem. Soc. Rev. 1993, 347-359.
9. Reviews and books: (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237-1286;
10. (b) Curran, D. P. Synthesis 1988, 417-439 and 489-513;
11. (c) Curran, D. P. Synlett 1992, 943-961;
12. (d) Malacria, M. Chem. Rev. 1996, 96, 289-306;
13. (e) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986;
14. (f) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
15. (a) Srikishna, A.; Danieldoss, S. J. J. Org. Chem. 1997, 62, 7863-7865;
16. (b) Osaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705-2708, and references cited therein;
17. (c) Gassman, P. G.; Lee, C. J. J. Am. Chem. Soc. 1989, 111, 739-740;
18. (d) Weng, W. V; Luh, T.-Y. J. Org Chem. 1993, 58, 5574-5575;
19. (e) Zhang, W.; Dowd, P. Tetrahedron Lett. 1992, 33, 7307-7310;
20. (f) Journet, M.; Malacria, M. J. Org. Chem. 1994, 59, 718-719;
21. (g) Denis, R. C.; Rancourt, J.; Ghiro, E.; Boutonnet, F.; Gravel, D. Tetrahedron Lett. 1993, 34, 2091-2094;
22. (h) Denis, R. C.; Gravel, D. Tetrahedron Lett. 1994, 35, 4531-4534;
23. (i) Devin, P.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1998, 63, 6764-6765;
24. (j) Srikishna, A.; Sharma, G. V. R. J. Chem. Soc., Perkin Trans. 1 1997, 177-181;
25. (k) Ferjancik, Z.; Saicic, R. N.; Cekovic, Z. Tetrahedron Lett. 1997, 38, 4165-4168;
26. (l) Warner, C. R.; Strunk, R. J.; Kuivila, H. G. J. Org. Chem. 1966, 31, 3381-3384;
27. (m) Halgren, T. A.; Howden, M. E. H.; Roberts, J. D. J. J. Am. Chem. Soc. 1967, 89, 3051-3052.
28. 2-mediated reaction, the uncyclised direct reductionproduct 1c was selectively obtained. Since the equilibration between 5 and 6 is fast compared to hydrogen abstraction fromtributyltin hydride and since, due to transition state polarisation effect, the presence of a carbalkoxy substituent does notappreciably change the rate of hydrogen abstraction from tributyltin hydride by alkyl radicals (Newcomb, M.; Horner, J. H.; Filipowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674-3684), these preliminary observations, which would need further more detailed analysis, seem to indicate that the equilibrium between 5 and 6 is largely in favourof 5.
29. 2-mediated reaction, the uncyclised direct reduction product 1c was selectively obtained. Since the equilibration between 5 and 6 is fast compared to hydrogen abstraction from tributyltin hydride and since, due to transition state polarisation effect, the presence of a carbalkoxy substituent does not appreciably change the rate of hydrogen abstraction from tributyltin hydride by alkyl radicals (Newcomb, M.; Horner, J. H.; Filipowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674-3684), these preliminary observations, which would need further more detailed analysis, seem to indicate that the equilibrium between 5 and 6 is largely in favourof 5.
30. 2-mediated reaction, the uncyclised direct reductionproduct 1c was selectively obtained. Since the equilibration between 5 and 6 is fast compared to hydrogen abstraction fromtributyltin hydride and since, due to transition state polarisation effect, the presence of a carbalkoxy substituent does notappreciably change the rate of hydrogen abstraction from tributyltin hydride by alkyl radicals (Newcomb, M.; Horner, J. H.; Filipowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674-3684), these preliminary observations, which would need further more detailed analysis, seem to indicate that the equilibrium between 5 and 6 is largely in favour of 5.
31. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921; see, also: Choi, S.-Y.; Toy, P. H.; Newcomb, M. J. Org. Chem. 1998, 63, 8609-8613.
32. Newcomb, M.; Johnson, C. C.; Manek, M. B.; Varick, T. R. J. Am. Chem. Soc. 1992, 114, 10915-10921; see, also: Choi, S.-Y.; Toy, P. H.; Newcomb, M. J. Org. Chem. 1998, 63, 8609-8613.