Formation of non-racemic tricyclic compounds by intramolecular 1,3-dipolar cycloaddition of nitrones

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 841-844

  Aurich, Hans Günter ^a   Geiger, Michael ^a   Gentes, Christian ^a   Köster, Heiner ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE; POLYCYCLIC HYDROCARBON;

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

EID: 0030043908     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02275-9     Document Type: Article

References (17)

1. a) Tuffariello, J.J. In 1.3-Dipolar Cycloaddition Chemistry; Padwa A. Ed.; Wiley Interscience: New York 1984; Chapter 9, pp. 116-119.
2. b) Wade, P.A. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I.; Semmelhack, M.F. Eds., Pergamon: Oxford 1991, Vol.4, pp. 1113-1114.
3. LeBel, N.A. Trans. N.Y. Acad. Sci. 1965, 27, 858-867, (C.A. 1966, 64, 548h).
4. LeBel, N.A. Trans. N.Y. Acad. Sci. 1965, 27, 858-867, (C.A. 1966, 64, 548h).
5. Walts, A.E.; Roush, W.R. Tetrahedron 1985, 41, 3463-3478.
6. Stanssens, D.; De Keukeleire, D.; Vandewalle, M. Tetrahedron Asymm. 1990, 1, 547-560.
7. a) Wollenberg, R.H.; Goldstein, J.E. Synthesis 1980, 757-758.
8. b) Knight, J.; Parsons, P.J. J. Chem. Soc., Perkin Trans 1, 1989, 979-984.
9. c) Curran, D.P.; Jacobs, P.B. Tetrahedron Lett. 1985, 26, 2031-2034.
10. Hassner, A.; Murthy, K.S.K.; Padwa A.; Chiacchio, U.; Dean, D.C.; Schoffstall, A.M. J. Org. Chem. 1989, 54, 5277-5286.
11. Tamura, O.; Okabe, T.; Yamaguchi, T.; Gotanda, K.; Noe, K.; Sakamoto, M. Tetrahedron 1995, 51, 107-118.
12. After preparation of the manuscript a paper appeared describing tetracyclic compounds which are similar to 12 and 13, insofar as they contain the same tricyclic frame but an additional oxygen atom in the six-membered ring: Hewson, A.T.; Jeffery, J.; Sczcur, N. Tetrahedron Lett. 1995, 36, 7731-7734.
13. Using 1-bromo-2-cyclohexene instead of allyl bromide the same reaction procedures were followed as described before for the preparation of the corresponding bicyclic compounds: Aurich, H.G.; Biesemeier, F. Synthesis 1995, 1171-1178 (X = O); Aurich, H.G.; Gentes, C.; Harms, K. Tetrahedron 1995, 51, 10497-10512 (X = NR).
14. Using 1-bromo-2-cyclohexene instead of allyl bromide the same reaction procedures were followed as described before for the preparation of the corresponding bicyclic compounds: Aurich, H.G.; Biesemeier, F. Synthesis 1995, 1171-1178 (X = O); Aurich, H.G.; Gentes, C.; Harms, K. Tetrahedron 1995, 51, 10497-10512 (X = NR).
15. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 2411-2431.
16. The results of the X-ray analysis performed by Dr. K. Harms will be published later.
17. To the best of our knowledge only one example of two trans-fused five-membered rings containing an isoxazolidine moiety comparable to 13C has been described: Armstrong, P; Grigg, R.; Heaney, F.; Surendrakumar, S.; Warnock, W.J. Tetrahedron 1991, 47, 4495-4518.