4182
B. Colman et al. / Tetrahedron: Asymmetry 10 (1999) 4175–4182
Acknowledgements
We thank the EPSRC and Lancaster Synthesis for a CASE award (to TDT) and the EPSRC for a grant
(to SEdS).
References
1. O’Brien, P.; Poumellec, P. Tetrahedron Lett. 1996, 37, 8057–8058; O’Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans.
1 1998, 2435–2441.
2. Bhuniya, D.; DattaGupta, A.; Singh, V. K. J. Org. Chem. 1996, 61, 6108–6113.
3. For reviews, see: O’Brien, P. J. Chem. Soc., Perkin Trans. 1 1998, 1439–1457; Hodgson, D. M.; Gibbs, A. R.; Lee, G. P.
Tetrahedron 1996, 52, 14361–14384.
4. For recent examples, see: Asami, M.; Ogawa, M.; Inoue, S. Tetrahedron Lett. 1999, 40, 1563–1564; Södergen, M. J.;
Andersson, P. G. J. Am. Chem. Soc. 1998, 120, 10760–10761.
5. For a preliminary communication of some of this work, see: de Sousa, S. E.; O’Brien, P.; Steffens, H. C. Tetrahedron Lett.
1999, 40, in press.
6. O’Brien, P.; Poumellec, P. Tetrahedron Lett. 1996, 37, 5619–5622; de Sousa, S. E.; O’Brien, P. Tetrahedron Lett. 1997,
38, 4885–4888; de Sousa, S. E.; O’Brien, P.; Poumellec, P. Tetrahedron: Asymmetry 1997, 8, 2613–2618; de Sousa, S. E.;
O’Brien, P.; Poumellec, P. J. Chem. Soc., Perkin Trans. 1 1998, 1483–1492.
7. Dieter, R. K.; Lagu, B.; Dieter, J. W.; Deo, N.; Pennington, W. T. Synlett 1990, 109–110; Dieter, R. K.; Deo, N.; Lagu, B.;
Dieter, J. W. J. Org. Chem. 1992, 57, 1663–1671.
8. Soai, K.; Yokoyama, S.; Hayasaka, T. J. Org. Chem. 1991, 56, 4264–4268.
9. Anderson, S. R.; Ayers, J. T.; De Vries, K. M.; Ito, F.; Mendenhall, D.; Vanderplas, B. C. Tetrahedron: Asymmetry 1999,
10, 2655–2663.
10. Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157–6163; Lamant, M.; Guignard, A. Helv. Chim. Acta 1987,
70, 1279–1285; Oppolzer, W.; Tamura, O.; Sundarababu, G.; Signer, M. J. Am. Chem. Soc. 1992, 114, 5900–5902; Bonar-
Law, R. P.; Davis, A. P.; Dorgan, B. J.; Reetz, M. T.; Wehrsig, A. Tetrahedron Lett. 1990, 31, 6725–6728; Kreutz, O. C.;
Moran, P. J. S.; Rodrigues, J. A. R. Tetrahedron: Asymmetry 1997, 8, 2649–2653; Koga, K.; Yamada, S.-i. Chem. Pharm.
Bull. 1972, 20, 539–542; Claremon, D. A.; Lumma, P. K.; Phillips, B. T. J. Am. Chem. Soc. 1986, 108, 8265–8266; Jackson,
W. R.; Jacobs, H. A.; Jayatilake, G. S.; Matthews, B. R.; Watson, K. G. Aust. J. Chem. 1990, 43, 2045–2062; Boerner, A.;
Krause, H. Tetrahedron Lett. 1989, 30, 929–930; Boerner, A.; Krause, H. J. Prakt. Chem. 1990, 332, 307–312.
11. Grunewald, G. L.; Ye, Q. J. Med. Chem. 1988, 31, 1984–1986; Fodor, G.; Bruckner, V.; Kiss, J.; Ohegyi, G. J. Org. Chem.
1949, 14, 337–345.
12. Brauch, F.; Dralle, H.; Blanka, H. J. Ger. Patent 3408 850, 1984; Chem. Abstr. 1985, 102, 24270; Herrmann, R. In
Stereoselective Synthesis, Houben-Weyl; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; 1996; Vol.
9, pp. 5780–5785.
13. Tlahuext, H.; Contreras, R. Tetrahedron: Asymmetry 1992, 6, 727–730.
14. For related examples, see: Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1993, 1375–1376;
Okuda, M.; Tomioka, K. Tetrahedron Lett. 1994, 35, 4585–4586; Lipshutz, B. H.; Miller, T. A. Tetrahedron Lett. 1990,
31, 5253–5256.
15. Fitton, A. O.; Frost, J. R. J. Chem. Soc., Perkin Trans. 1, 1974, 1153–1154; Ardabilchi, N.; Fitton, A. O.; Frost, J. R.;
Oppong-Boachie, F. K.; Hadi, A. B. A.; Sharif, A. B. M. J. Chem. Soc., Perkin Trans. 1 1979, 539–543.
16. Oussaid, B.; Berlan, J.; Soufiaoui, M.; Garrigues, B. Synth. Commun. 1995, 25, 659–665.
17. Kniezo, L.; Kristian, P.; Budesinsky, M.; Havrilova, K. Collect. Czech. Chem. Commun. 1981, 46, 717–728.
18. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543–2549.