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

Tetrahedron

Volumn 54, Issue 13, 1998, Pages 3181-3196

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

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; AMPHOLYTE; BENZALDEHYDE DERIVATIVE; BICYCLO COMPOUND; DECANE; TRICYCLIC AROMATIC COMPOUND; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOMER; MOLECULAR INTERACTION; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS;

EID: 0032568353     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00064-7     Document Type: Article

References (23)

1. 1. Tufariello, J.J. in 1.3 Dipolar Cycloaddition Chemistry, Padwa, A. (Ed.), Wiley - Interscience: New York, 1984, Chapter 9, pp. 116-122, 140-153;
2. b) Wade, P.A. in Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I; Semmelhack, M.F. Eds., Pergamon: Oxford 1991, Vol. 4, pp. 1113-1124;
3. c) Breuer, E. in Nitrones, Nitronates and Nitroxides, Patai, S.; Rappoport, Z. Eds.; Wiley: Chichester 1989, pp. 182-186, 264-277;
4. d) Torsell, K.B.G. Nitrile Oxides, Nitrones, and Nitronates, VCH Publishers Inc.: Weinheim 1988, pp. 194-254.
5. 2. LeBel, N.A. Trans. N.Y. Acad Sci. 1965, 27, 858-867, (C.A. 1966, 64, 548h).
6. 3. a) Walts, A.E.; Roush, W.R. Tetrahedron 1985, 41, 3463-3478;
7. b) Stanssens, D.; De Keukeleire, D.; Vandewalle, M. Tetrahedron Asymm. 1990, 1, 547-560;
8. c)Tamura, O.; Okabe, T.; Yamaguchi, T.; Gotanda, K.; Noe, K., Sakamoto, M. Tetrahedron 1995, 51, 107-118.
9. 4. a) Hassner, A.; Maurya, R.; Friedman, O.; Gottlieb, H.E.; Padwa, A.; Austin, D. J. Org. Chem. 1993, 58, 4539-4546;
10. b) Chiacchio, U.; Casuscelli, F.; Corsaro, A.; Librando, V.; Rescifina, A.; Romeo, R.; Romeo, G. Tetrahedron, 1995, 51, 5689-5700;
11. c) see also references 6-16 in Aurich, H.G.; Biesemeier, F. Synthesis 1995, 1171-1178.
12. 5. a) Aurich, H.G.; Biesemeier, F. Synthesis 1995, 1171-1178;
13. b) Aurich, H.G.; Gentes, C.; Harms, K. Tetrahedron 1995, 51, 10497-10512;
14. c) Aurich, H.G.; Biesemeier, F.; Geiger, M.; Harms, K. Liebigs Ann./Recueil 1997, 423-434;
15. d) Aurich, H.G.; Geiger, M.; Sievers, U. Synlett 1997, 1004-1006. - See also references cited in 5a-d.
16. 6. Preliminary communication: Aurich, H.G; Geiger, M.; Gentes, C.; Köster, H. Tetrahedron Lett. 1996, 37, 841-844.
17. 7. a) Aurich, H.G; Frenzen, G.; Gentes, C. Chem. Ber. 1993, 126, 787-795;
18. b) Aurich, H.G.; Biesemeier, F.; Boutahar, M. Chem. Ber. 1991, 124, 2329-2334.
19. 8. Concerning allylic 1,3-strain see: Hoffmann, R.W. Chem. Rev. 1989, 89, 1841-1860.
20. 9. The atomic coordinates and additional data such as bond lengths and angles for this work are available on request from the Director of the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW. Any request should be accompanied by the full literature citation for this communication.
21. 10. Hesse, M., Meier, H., Zeeh, B. Spektroskopische Methoden in der organischen Chemie. Thieme: Stuttgart, 1991, p. 105.
22. 11. See also references 5b and c.
23. 12. Aurich, H.G.; Köster, H. Tetrahedron 1995, 51, 6285-6292, see also ref. 5b and 5c.