Synthesis of 2-aza-3-oxatetracyclo[7.3.1.17,11.02,6]tetradecane derivatives by the 1,3-dipolar cycloaddition reaction of homoadamantane-incorporated nitrones with alkenes

Tetrahedron

Volumn 53, Issue 15, 1997, Pages 5413-5422

  Yu, Yang ^a,c   Ohno, Masatomi ^a   Eguchi, Shoji ^a   Kawai, Takashi ^b   Terada, Yukimasa ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b MEIJO UNIVERSITY   (Japan)

^c SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030979105     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00236-6     Document Type: Article

References (13)

1. Synthesis of Novel Carbo-and Heteropolycycles. 46. For 45, see Eguchi, S.; Ishiura, K.; Okawa, T. Heterocyclic Commun., in press. For 44, see Okawa, T.; Sugimori, T.; Eguchi, S.; Kakehi, A. Chem. Lett., 1996, 843.
2. Synthesis of Novel Carbo-and Heteropolycycles. 46. For 45, see Eguchi, S.; Ishiura, K.; Okawa, T. Heterocyclic Commun., in press. For 44, see Okawa, T.; Sugimori, T.; Eguchi, S.; Kakehi, A. Chem. Lett., 1996, 843.
3. a) Tufariello, J.J. in 1,3-Dipolar Cycloaddition Chemistry; ed. by Padwa, A.; John Wiley and Sons, New York, 1988; Vol. 2, Chapter 9.
4. b) Brener, B; Aurich, H.G.; Nielsen, A. in Nitrones, Nitronates and Nitroxides; ed. by Patai, S.; John Wiley and Sons; New York, 1989; pp 139-312.
5. c) Little, R.D. in Comprehensive Organic Synthesis; ed by Trost, B.M.; Fleming, I.; Paquette, L. A. (Vol. ed.); Pergamon Press, Oxford, 1991; Vol. 5, 3.1.
6. Yu, Y.; Ohno, M.; Eguchi, S. Tetrahedron Lett. 1991, 32, 4965.; Tetrahedron 1993, 49, 823 .
7. Yu, Y.; Ohno, M.; Eguchi, S. Tetrahedron Lett. 1991, 32, 4965.; Tetrahedron 1993, 49, 823 .
8. Yu, Y.; Watanabe, N.; Ohno, M.; Eguchi, S. J.Chem. Soc. Perkin Trans. 1 1995, 1417.
9. Yu, Y.; Ohno, M.; Eguchi, S. J. Chem. Soc. Chem. Commun. 1994, 331.
10. Yu, Y.; Ohno, M.; Eguchi, S. Heterocyclic Commun. 1995, 1, 307.
11. Stewart, J.J.P. J. Comput.-Aid. Mol. Des. 1990, 4, 1 .
12. The validity of our transition state models - 3at and 4at, for example, was ascertained by the whole optimization with the TS key word. There was essentially no difference between the models and the optimized structures in the geometry of assembling isoxazolidine ring and in the HOMO and LUMO electron distributions.
13. AVS/Chemistry Viewer, Molecular Simulations, Inc., Pasadena, USA.