Synthesis of heterocycles. Construction of the 1-azabicyclo[2.2.1]heptyl system by sequential ring-closure of acylic β-ammonio substituted radicals

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5805-5808

  Della, Ernest W ^a   Knill, Andrew M ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030570883     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01231-2     Document Type: Article

References (6)

1. 1. Della, E. W.; Knill, A. M. J. Org. Chem. submitted for publication.
2. 2. As far as we are aware the only related positively-charged nitrogen-containing radicals that have been employed in radical cyclisations are the aminium cation radicals described by Newcomb and Deeb (see, eg, Newcomb, M.; Deeb, T. M. J. Am. Chem. Soc., 1987, 109, 3163-3164); interestingly, although these nitrogen-centred radicals are significantly different from those involved in this work, they yield β-ammonio substituted radicals upon cyclisation.
3. 3. Ho, T. L. Synthesis, 1972, 702-703.
4. 4. For leading references see Boelsterli, J.; Eggnauer, U.; Pombo-Villar, E.; Weber, H.-P.; Walkinshaw, M.; Gould, R. O. Helv. Chim. Acta, 1992, 75, 507-512, refs 2(a)-2(k). Cottrell, I. F.; Hands, D.; Kennedy, D. J.; Paul, K. J.; Wright, S. H. B.; Hoogsteen, K. J. Chem. Soc. Perkin Trans I, 1991, 1091-1097, refs 1-3.
5. 4. For leading references see Boelsterli, J.; Eggnauer, U.; Pombo-Villar, E.; Weber, H.-P.; Walkinshaw, M.; Gould, R. O. Helv. Chim. Acta, 1992, 75, 507-512, refs 2(a)-2(k). Cottrell, I. F.; Hands, D.; Kennedy, D. J.; Paul, K. J.; Wright, S. H. B.; Hoogsteen, K. J. Chem. Soc. Perkin Trans I, 1991, 1091-1097, refs 1-3.
6. 13C NMR spectra were in accord with the designated structures.