Regioselective 6-endo cyclization of 5-carbomethoxy-5-hexenyl radicals: A convenient synthesis of derivatives of the 1-azabicyclo[2.2.1]heptyl system

Organic Letters

Volumn 1, Issue 3, 1999, Pages 363-365

  Della, Ernest W ^a   Kostakis, Chris ^a   Smith, Paul A ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000855014     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990557n     Document Type: Article

References (16)

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4. (d) Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
5. (e) Julia, M. Acc. Chem. Res. 1971, 4, 386.
6. (e) Giese, B. Radicals. In Organic Synthesis: Formation of Carbon Carbon Bonds; Baldwin, J. E., Ed.; Pergamon: New York, 1986.
7. Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun. 1974, 472.
8. Microanalytical and spectral characterization of the half ester 12 and all intermediate compounds involved in its synthesis from 2-carbomethoxy-cyclohexanone will be presented in the full paper.
9. For leading reference, see: Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
10. (a) Della, E. W.; Smith, P. A. J. Org. Chem. 1999, 64, 2110.
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12. (c) Della, E. W.; Knill, A. M. Tetrahedron Lett. 1996, 37, 5805.
13. (d) Della, E. W.; Knill, A. M. J. Org. Chem. 1996, 61, 7529.
14. For leading reference, see: Jenkins, S. M.; Wadsworth, H. J.; Bromidge, S.; Orlek, B. S.; Wyman, P. A.; Riley, G. J.; Hawkins, J. J. Med. Chem. 1992, 35, 2392.
15. Mattocks, A. R. J. Chem. Soc., Perkin Trans. 2 1978, 896.
16. Full characterization of 21 and 17 will be presented in the full paper.