Intermolecular additions of cyclobutanone derived radicals. A convergent, highly efficient access to polycyclic cyclobutane containing structures

Tetrahedron Letters

Volumn 44, Issue 42, 2003, Pages 7703-7706

  Binot, Grégori ^a   Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

Cyclobutanones; Intramolecular Horner Emmons reaction; Radical additions; Xanthate transfer

Indexed keywords

CYCLOBUTANE; CYCLOBUTANONE DERIVATIVE; CYCLOHEPTENE; CYCLOHEXENE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; POLYCYCLIC HYDROCARBON; RADICAL;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; HORNER REACTION; HORNER WADSWORTH EMMONS REACTION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0141794089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.042     Document Type: Article

References (27)

1. Namyslo J.C., Kaufmann D.E. Chem. Rev. 103:2003;1485-1538. and references there cited therein.
2. Lee-Ruff E. Halton B. Advances in Strain in Organic Chemistry. 1:1991;167-213 JAI Press, Greenwich, CT.
3. Bellus D., Ernst B. Angew. Chem., Int. Ed. Engl. 27:1988;797-827.
4. Snider B.B. Chem. Rev. 88:1988;793-811.
5. Mehta G., Rao H.S.P. Synth. Commun. 15:1985;991-1000.
6. Brady W.T. Synthesis. 1971;8415-8422.
7. Kagan H.B. Ann. Chim. 10:1965;203-212.
8. Lee-Ruff E., Maldenova G. Chem. Rev. 103:2003;1449-1484. and references there cited therein.
9. Orr R.K., Calter M.A. Tetrahedron. 59:2003;3545-3566.
10. Nemoto H., Fukumoto K. Synlett. 1996;863-875.
11. Genicot C., Ghosez L. Tetrahedron Lett. 33:1992;7357-7360.
12. Medarde M., López J.L., Morillo M.A., Tomé F., Adeva M., San Feliciano A. Tetrahedron Lett. 36:1995;8097-8098.
13. Poss A.J., Belter R.K. J. Org. Chem. 52:1987;4810-4812.
14. Conia J.-M., Goré J. Bull. Soc. Chim. Fr. 1964;1968-1975.
15. Dowd P., Zhang W. J. Org. Chem. 57:1992;7163-7171.
16. Zard S.Z. Angew. Chem., Int. Ed. Engl. 36:1997;672-685.
17. Quiclet-Sire B., Zard S.Z. Phosphorus, Sulfur and Silicon. 153-154:1999;137-154.
18. Zard S.Z. Renaud P., Sibi M.P. Radicals in Organic Synthesis. 1:2001;90-108 Wiley-VCH, Weinheim.
19. Reuss R.H., Hassner A. J. Org. Chem. 39:1974;1785-1787.
20. Liard A., Quiclet-Sire B., Zard S.Z. Tetrahedron Lett. 37:1996;5877-5880.
21. Quiclet-Sire B., Quintero L., Sanchez-Jimenez G., Zard S.Z. Synlett. 2003;75-78.
22. Binot G., Quiclet-Sire B., Saleh T., Zard S.Z. Synlett. 2003;382-386.
23. Cholleton N., Gillaizeau-Gauthier I., Six Y., Zard S.Z. Chem. Commun. 2000;535-536.
24. For another case where the O-neopentyl xanthate proved superior, see: Quiclet-Sire B., Zard S.Z. J. Am. Chem. Soc. 118:1996;9190-9191.
25. Broom N., O'Hanlon P.J., Simpson T.J., Stephen R., Willis C.L. J. Chem. Soc., Perkin Trans. 1. 1995;3067-3072.
26. See for example: (a) Brocksom, T. J.; Coelho, F.; Deprés, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 15313-15325 and references there cited; (b) Biswas, S.; Gosh, A.; Venkateswaran, R. V. J. Org. Chem. 1990, 55, 3498-3502.
27. See for example: (a) Brocksom, T. J.; Coelho, F.; Deprés, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 1996, 118, 15313-15325 and references there cited; (b) Biswas, S.; Gosh, A.; Venkateswaran, R. V. J. Org. Chem. 1990, 55, 3498-3502.