Exclusively endo-selective Lewis acid-catalyzed hetero Diels-Alder reactions of (E)-1-phenylsulfonyl-3-alken-2-ones with vinyl ethers

Tetrahedron

Volumn 52, Issue 4, 1996, Pages 1205-1220

  Wada, Eiji ^a   Pei, Wen ^a   Yasuoka, Hiroshi ^a   Chin, Uchou ^a   Kanemasa, Shuji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030068385     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00980-9     Document Type: Article

References (28)

1. (a) Wada, E.; Kanemasa, S.; Tsuge, O. Chem. Lett. 1989, 675-678.
2. (b) Wada, E.; Kanemasa, S.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 860-868.
3. (a) Boquel, P.; Chapleur, Y. Tetrahedron Lett. 1990, 31, 1869-1872.
4. (b) Tursch, B.; Chome, C.; Braekman, J. C. Bull. Soc. Chim. Belg. 1973, 82, 699-702.
5. (c) Longley, R. I. Jr.; Emerson, W. S. J. Am. Chem. Soc. 1950, 72, 3079-3081.
6. (a) Hall, S. S.; Weber, G. F.; Duggan, A. J. J. Org. Chem. 1978, 43, 667-672. A lanthanoid catalyst is an effective catalyst in the Diels-Alder reactions of 2-alkenals:
7. (b) Chapleur, Y.; Euvrard, M. -N. J. Chem. Soc. Chem. Commun. 1987, 884-885.
8. (c) Danishefsky, S.; Bednarski; Bednarski, M. Tetrahedron Lett. 1984, 25, 721-724.
9. (a) Boger, D. L.; Weinreb, S.M. "Hetero Diels-Alder Methodology in Organic Synthesis," as Vol. 47 of "Organic Chemistry, A Series of Monographs," ed by Wasserman, H. H. , Academic Press, San Diego (1987), Chap. 7, pp. 167-213.
10. (b) Schmidt, R. R. Acc. Chem. Res., 1986, 19, 250-259.
11. (c) Tietze, L. F. "Selectivity - a Goal for Synthetic Efficiency," ed by Bartmann, W.; Trost, B. M., Verlag Chemie GmbH, Weinheim (1984), pp 299-316.
12. (d) G. Desimoni and G. Tacconi, Chem. Rev 75, 651-692 (1975).
13. Catalyzed intramolecular asymmetric hetero Diels-Alder reactions: Tietze, L. F.; Saling, P. Synlett. 1992, 281-282.
14. As preliminary works: (a) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 145-148.
15. (b) Wada, E.; Yasuoka, H.; Kanemasa, S. Chem. Lett. 1994, 1637-1640.
16. Belletire, J. L.; Spletzer, E. G. Synth. Commun. 1987, 17, 1701-1707.
17. John, R. A.; Schmid, V.; Wyler, H. Helv. Chim. Acta. 1987, 70, 600-606.
18. (a) Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1994, 116, 3949-3950.
19. (b) Mori, A.; Ishihara, K.; Yamamoto, H. Tetrahedron Lett. 1986, 27, 987-990.
20. Steven, V. L.; Lygo, B.; Sternfeld, F.; Wonnacott, A. Tetrahedron. 1986, 42, 4333-4342.
21. Oxley, P.; Partridge, M. W.; Robson, T. D.; Short, W. F. J. Chem. Soc. 1946, 763-771.
22. Tavares, D. F.; O'sullivan, W. I.; Hauser, C. R. J. Org. Chem. 1962, 27, 1251-1254.
23. (a) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954.
24. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340-5345 and references cited therein.
25. Subramanyam, V.; Silver, E. H.; Soloway, A. H. J. Org. Chem. 1976, 41, 1272-1273.
26. (a) Baldwin, J. E.; Walker, L. E. J. Org. Chem. 1966, 31, 3985-3989.
27. (b) Miller, S. I. J. Am. Chem. Soc. 1956, 78, 6091-6095.
28. Lansbury, P. T.; Bebernitz, G. E.; Maynard, S. C.; and Spsgnolo, C. J. Tetrahedron Lett. 1985, 26, 169-172.