Intramolecular [2 + 2] cycloadditions of ketenes and keteniminium salts to olefins

Journal of the American Chemical Society

Volumn 107, Issue 7, 1985, Pages 2192-2194

  Markó, István ^a   Ronsmans, Bruno ^a   Hesbain Frisque, Anne Marie ^a   Dumas, Stéphane ^a   Ghosez, Léon ^a   Ernst, Beat ^b   Greuter, Hans ^b  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001649302     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00293a073     Document Type: Article

References (9)

1. For selected examples, see: (a) Martin, P.; Greuter, H.; Bellus, D.; Helv. Chim. Acta 1981, 64, 64. (b) Brady, W. T. Tetrahedron 1981, 37, 2949. (c) Newton, R. F.; Roberts, S. M. Tetrahedron 1980, 2163. (d) Goldstein, S.; Vannes, P.; Houge, C.; Frisque-Hesbain, A. M.; Wiaux-Zamar, C.; Ghosez, L. J. Am. Chem. Soc. 1981, 103 4616.
2. Trost, B. M.; Preckel, M.; Leichter, L. M. J. Am. Chem. Soc. 1975, 97, 2224.
3. Ghosez, L. “Stereoselective Synthesis of Natural Products”; Bartmann, W., Winterfeldt, E., Eds.; Excerpta Medica: Amsterdam—Oxford, 1979; pp 93–105. (b) Michel, P.; O'Donnell, M. J.; Hesbain-Frisque, A. M.; Ghosez, L.; Declercq, J. P.; Germain, G.; Van Meerssche, M.; Tetrahedron Lett. 1980, 2577.
4. Recent review: Ghosez, L.; O'Donnell, M. J. “Pericyclic Reactions”; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. 2, pp 79–140.
5. Ghosez, L.; Marchand-Brynaert, J. “Iminium Salts in Organic Chemistry Part 1; Böhme, J., Viehe, H. G., Eds., Wiley: New York, 1976; pp 421–532. (b) Falmagne, J. B.; Escudero, J.; Taleb-Sahraoui, S.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1981, 20, 879. Beereboom, J. J. J. Am. Chem. Soc. 1963, 85, 3525; J. Org. Chem. 1965, 30, 4230. (b) Erman, W. F. J. Am. Chem. Soc. 1969, 91, 779. (c) Baldwin, S. W.; Page, E. H., Jr. J. Chem. Soc., Chem. Commun. 1972, 1337. (d) Leyendecker, F.; Bloch, R.; Conia, J. M. Tetrahedron Lett. 1972, 3703. (e) Bisceglia, R. H.; Cheer, C. J. J. Chem. Soc., Chem. Commun. 1973, 165. (f) Leyendecker, F. Tetrahedron 1976, 32, 349. (g) Maujean, A.; Marcy, G.; Chuche, J. J. Chem. Soc., Chem. Commun. 1980, 92. (h) Kuzuya, M.; Miyake, F.; Okuda, T. Tetrahedron Lett. 1980, 1043 and 2185. Alder, A.; Bellus, D. J. Am. Chem. Soc. 1983, 105, 6712.
6. Erman, W. F. J. Am. Chem. Soc. 1967, 89, 3828. (b) Chapman, O. L.; Lassila, J. D. J. Am. Chem. Soc. 1968, 90, 2449. (c) Chapman, O. L.; Kane, M.; Lassila, J. D.; Loeschen, R. L.; Wright, H. E. J. Am. Chem. Soc. 1969, 91, 6856. (d) Kende, A. S.; Goldschmit, Z.; Izzo, P. T. J. Am. Chem. Soc. 1969, 91, 6858. (e) Sauers, R. R.; Kelly, K. W. J. Org. Chem. 1970, 35, 3286. (f) Hart, H.; Love, G. M. J. Am. Chem. Soc. 1971, 93, 6266. (g) Becker, D.; Nagler, M.; Birnbaum, D. J. Am. Chem. Soc. 1972, 94, 4771. (h) Goldschmidt, Z.; Gutman, U.; Bakal, Y.; Worchel, A. Tetrahedron Lett. 1973, 3759. (i) Becker, D.; Harel, Z.; Birnbaum, D. J. Chem. Soc., Chem. Commun. 1975, 377. (j) Ayral-Kaloustian, S.; Wolff, S.; Agosta, W. C. J. Org. Chem. 1978, 43, 3314. (k) Becker, D.; Birnbaum, D. J. Org. Chem. 1980, 45, 570. (1) Ireland, R. E.; Godfrey, J. D.; Thaisrivongs, S. J. Am. Chem. Soc. 1981, 103, 2446. (m) Lee-Ruff, E.; Hopkinson, A. C.; Kazarians-Moghaddam, H. Tetrahedron Lett. 1983, 2067. (n) Schultz, A. G.; Dittami, J. P.; Eng, K. K. Tetrahedron Lett. 1984, 1255.
7. Snider, B. B.; Hui, R. A. H. F.; Kulkarni, Y. S. J. Am. Chem. Soc., following paper in this issue.
8. 13C NMR, and mass spectra or elemental analysis. Saimoto, H.; Houge, C.; Hesbain-Frisque, A. M.; Mockel, A.; Ghosez, L. Tetrahedron Lett. 1983, 2251.
9. Houge, C.; Frisque-Hesbain, A. M.; Mockel, A.; Ghosez, L. J. Am. Chem. Soc. 1982, 104 2920.