Stereochemistry and mechanisms of thermal cycloaddition reactions of conjugated enynes. The stereospecific formation of six tetrahedral centers in a single reaction

Tetrahedron Letters

Volumn 37, Issue 10, 1996, Pages 1559-1562

  Ionescu, Dumitru ^a   Silverton, James V ^b   Dickinson, L Charles ^a   Miller, Bernard ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029935367     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00103-7     Document Type: Article

References (20)

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2. Michael, A.; Bucher, J. E. Ber. Deutsch. Chem. Ges. 1895, 28, 2511; Am. Chem. J. 1898, 20, 89.
3. For refs., see ref. 3 and Onischenko, A. S., Diene Synthesis, Daniel Davey & Co., Inc., New York, 1964, pgs. 249-254, 635-637.
4. Danheiser, R. L.; Gould, A. E.; Fernandez de la Pradilla, R.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514.
5. Whitlock, H. W., Jr.; Wu, E.-M.; Whitlock, B. J. J. Org. Chem. 1969, 34, 1857.
6. Hoffmann, H. M. R., et al. Tetrahedron 1993, 49, 8999.
7. (a) Pfeiffer, P.; Möller, W. Chem. Ber. 1907, 40, 3859;
8. (b) Bossenbroek, B.; Sanders, P. C.; Curry, H. M.; Schechter, H. J. Am. Chem. Soc. 1969, 91, 371;
9. (c) Quast, H., et al. Chem. Ber. 1992, 125, 2591.
10. Alder, K., in Newer Methods of Preparative Organic Chemistry, Vol. I, Interscience Publishers, Inc., New York, 1948.
11. Miller, B.; Ionescu, D. Tetrahedron Lett. 1994, 35, 6615.
12. Dané, E.; Höss, O.; Bindseil, A. W.; Schmitt, J. Liebigs Ann. 1937, 532, 39; Dané, E.; Höss, O.; Eder, K.; Schmitt, J.; Schön, O. ibid. 1938, 536, 183.
13. Dané, E.; Höss, O.; Bindseil, A. W.; Schmitt, J. Liebigs Ann. 1937, 532, 39; Dané, E.; Höss, O.; Eder, K.; Schmitt, J.; Schön, O. ibid. 1938, 536, 183.
14. (a) Butz, L. W.; Gaddis, A. M.; Butz, E. W. J.; Davis, R. E. J. Org. Chem. 1940, 5, 379;
15. (b) Butz, L. W.; Joshel, L. M. J. Am. Chem. Soc. 1941, 63 , 3344;
16. (c) Joshel, L. M.; Butz, L. W.; Feldman, J. ibid. 1941, 63, 3348;
17. (d) Butz, L. W.; Joshel, L. M. ibid. 1942, 64, 1311;
18. (e) Nudenberg, W.; Butz, L. W. ibid. 1943, 65, 2059;
19. (f) Butz, L. W.; Gaddis, A. M.; Butz, E. W. J. ibid. 1947, 69, 92.
20. A PLUTO drawing of the structure of adduct 3 is shown below. Further details of the crystal structure investigation may be obtained from the Director of the Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ (UK) on quoting the full journal citation. (formula presented)