Reagent Design and Study of Allene as a Promising Class of Reagents (Synthons) for Cycloaddition. The Site Selective and Regioselective Diels-Alder Reactions of (Phenylsulfonyl)propadiene and Alkylation of the Adducts

Journal of Organic Chemistry

Volumn 50, Issue 4, 1985, Pages 512-517

  Hayakawa, Kenji ^a   Nishiyama, Hitoshi ^a   Kanematsu, Ken ^a  

^a Kyushu University 62 ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845377269     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00204a018     Document Type: Article

References (30)

1. (1) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavec, F.; White, C. T. “The Total Synthesis of Natural Products”; ApSimon, J., Ed.,; John Wiley: New York, 1983; Vol. 5.
2. (2) Taylor, D. R. Chem. Rev. 1967, 67, 317.
3. (3) Fleming, I. “Frontier Orbitals and Organic Chemical Reactions”; Wiley: New York, 1976.
4. (4) (a) Kurtz, P.; Gold, H.; Disselnkotter, H. Liebigs Ann. Chem. 1959, 624, 1. (b) Büchi, G.; Carlson, J. A. J. Am. Chem. Soc. 1968, 90, 5336. (c) Kozikowski, A. P.; Floyd, W. C.; Kuniak, M. P. Chem. Commun. 1977, 582. (d) Gommper, R.; Wolf, U. Liebigs Ann. Chem. 1979, 1388.
5. (5) (a) Hayakawa, K.; Mibu, N.; Osawa, E.; Kanematsu, K. J. Am. Chem. Soc. 1982 104, 7136. (b) Hayakawa, K.; Kamikawaji, Y.; Kanematsu, K. Tetrahedron Lett. 1982, 23, 2171.
6. (6) Stirling, C. J. M. J. Chem. Soc. 1964, 5856, 5863, 5875.
7. (7) Magnus, P. D. Tetrahedron 1977, 33, 2019.
8. (8) (a) Julia, M.; Righini-Tapie, A.; Verpeaux, J.-N. Tetrahedron 1983, 39, 3283. (b) Julia, M.; Verpeaux, J.-N. Tetrahedron 1983, 39, 3289.
9. (9) Hirama, M. Tetrahedron Lett. 1981, 22, 1905. (10) Veniard, L.; Benaim, J.; Pourcelot, G.; Normant, M.-H. C. R. Acad. Sci. Ser. C 1968, 1092.
10. (11) Guildford, A. J.; Turner, R. W. Chem. Commun. 1983, 466.
11. (12) Maccagnani, G.; Montanari, F.; Tadei, F. J. Chem. Soc. B 1968, 453. (13) Trost, B. M.; Arndt. H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 3477.
12. (14) Muller, C.; Schweig, A.Tetrahedron 1973, 29, 3973.
13. (15) Woodard, R. B.; Hoffmann, R. “The Conservation of Orbital Symmetry”; Academic Press: New York, 1970. (16) Carr, R. V. C.; Williams, R. V.; Paquette, L. A. J. Org. Chem. 1983, 48, 4976.
14. (17) Pinkerton, A. A.; Schwaezenbach, D. J. Am. Chem. Soc. 1981, 103, 2095.
15. (18) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328.
16. (19) Ciabattoni, L.; Anderson, H. W. Tetrahedron Lett. 1967, 3377.
17. (20) Gommper, R.; Studeneer, A.; Elser, W. Tetrahedron Lett. 1968, 1019.
18. (21) Truce, W. E.; Lin, C. I. M. J. Am. Chem. Soc. 1973, 95, 4426.
19. (22) (a) Iwasaki, T.; Kajigaeshi, S.; Kanemasa, S. Bull. Chem. Soc. Jpn. 1978, 51, 229. (b) Sanechika, K.; Kajigaeshi, S.; Kanemasa, S. Chem. Lett. 1977, 861. (c) Yamamoto, K.; Kajigaeshi, S.; Kanemasa, S. Chem. Lett. 1977, 85, 91.
20. (23) Liu, C.-Y.; Mareda, J.; Houk, K. N. J. Am. Chem. Soc. 1983, 105, 6714.
21. (24) Ciabattoni, J.; Cabell, M. Tetrahedron Lett. 1968, 2693.
22. (25) Mukherjee, D.; Watts, C. R.; Houk, K. N. J. Org. Chem. 1978, 43, 817.
23. (26) Kuroda, H.; Kumii, T. Theor. Chim. Acta 1967, 7, 220. (27) (a) Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4974. (b) Denmark, S. E.; Harmata, M. A. J. Org. Chem. 1983, 48, 3369.
24. (28) Ghosez, L.; O’Donnell, M. J. In “Pericyclic Reactions”; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. II.
25. (29) Hein, R. W.; Astle, M. J.; Schelton, J. R. J. Org. Chem. 1961, 26, 4874.
26. (30) Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161.
27. (31) Jung, M. E.; McCombs, C. A. Org. Synth. 1977, 58, 163.
28. (32) Danishefsky, S.; Kitahara, T.; Schuda, P. Org. Synth. 1980, 61, 147.
29. (33) Sanetica, K.; Kajigawase, S.; Kanemasa, S. Synthesis 1977, 202.
30. (34) Bullough, R. K.; Wheatley, P. J. Acta Crystallogr. 1957, 10, 233.