Organolithium additions to styrene derivatives, Part IV: Tandem intermolecular-intramolecular carbolithiation as a new route to tetralins

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6467-6470

  Wei, Xudong ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

STYRENE DERIVATIVE; TETRALIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030840477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01479-2     Document Type: Article

References (16)

1. Part I: Wei, X.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1996, 187.
2. Part II: Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1996, 37, 4209.
3. For an intramolecular styrene carbolithiation which proceeds by 5-exo-cyclisation at the styrene α-carbon see Bailey, W. F.; Khanolkar, A. D. Tetrahedron 1991, 47, 7727.
4. Part III: Wei, X.; Taylor, R. J. K. Tetrahedron: Asymmetry 1997, 8, 665.
5. (a) Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett 1995,1237;
6. (b) Baxter, A. D.; Murray, P. J.; Taylor, R. J. K. Tetrahedron Lett. 1992, 33, 2331;
7. (c) Davies, A. J.; Taylor, R. J. K.; Scopes, D. I. C.; Wadsworth, A. H. Bioorg. Med. Chem. Lett. 1992, 2, 481.
8. (a) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 2442;
9. (b) For more recent examples see Bailey, W. F.; Carson, M. W. Tetrahedron Lett. 1997, 38, 1329 and references therein;
10. (c) see also Koppang, M. D.; Ross, G. A.; Woolsey, N. F.; Bartak, D. E. J. Am. Chem. Soc. 1986, 108, 1441.
11. (a) Bailey, W. F.; Aspris, P. H. J. Org. Chem. 1995, 60, 754;
12. (b) Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080.
13. Substituted indane and indoline systems have been prepared by organolithium 5-exo-trig cyclisation processes: see references 6b and 6c and Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594.
14. Friedman, L.; Shani, A. J. Am. Chem. Soc. 1974, 96, 7101.
15. 13C NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
16. 32Si requires 288.2273 (3 ppm error)].