Studies in the stereoselective trapping of prochiral carbon radicals by optically active camphoxyl nitroxides

Tetrahedron Asymmetry

Volumn 8, Issue 19, 1997, Pages 3209-3212

  Braslau, Rebecca ^a   Burrill II, Leland C ^a   Chaplinski, Vladimir ^a   Howden, Rodney ^a   Papa, Patrick W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE; NITROXIDE;

ARTICLE; DRUG ISOLATION; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0030870442     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00426-6     Document Type: Article

References (11)

1. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Ang. Chem. Int. Ed. Eng. 1997, 36, 237-238.
2. Braslau, R.; Kuhn, H.; Burrill, L. C.; Lanham, K.; Stenland, C. J. Tetrahedron Lett. 1996, 37, 7933-7936.
3. Material derived from both (+) and (-)-camphene was utilized in this study, however all structures are drawn as coming from (-)-camphene for clarity.
4. 3) δ 143.3 (s), three of the following: [128.3 (d), 128.2 (d), 128.2 (d), 127.9 (d), 127.4 (d), 126.9 (d)], 100.6 (s), 80.9 (d), 78.7 (s), 68.4 (t), 51.0 (d), 45.8 (s), 42.8 (d), 36.7 (t), 29.6 (q), 28.2 (q), 24.9 (t), 23.5 (q), 23.1 (t), 22.5 (q), 21.6 (q).
5. n=15.0, 14.0 and 14.9 G respectively.
6. (a) Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629-1632.
7. (b) Arends, I. W. C. E.; Mulder, P.; Clark, K. B.; Wayner, D. D. M. J. Phys. Chem. 1995, 99, 8182-8189.
8. (c) Connolly, T. J.; Baldovi, M. V.; Mohtat, N.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4919-4922.
9. (d) Braslau, R.; Burrill, L. C.; Siano, M.; Naik, N.; Howden, R. K.; Mahal, L. K.; submitted for publication.
10. Fieser, L. F. and Fieser, M. Reagents for Organic Synthesis, Vol. 1, Wiley: New York, 1967; p. 135.
11. The typical broadening of NMR spectra by paramagnetic nitroxides is concentration dependent. It is possible that the sharp peaks seen here are due to a concentration effect, although as 9 mg of the sample were used in a 5 mm NMR tube, this is unlikely.