6062
Chem. 1999, 576, 300. (e) Hayashi, T. J. Organomet. Chem. 1999, 576, 195. (f) Wu, M.-Y., Yang, F.-Y.; Cheng, C.-H.
J. Org. Chem. 1999, 64, 2471.
3. For reviews on the additions of organometallic reagents to the CN bond, see: (a) Bloch, R. Chem. Rev. 1998, 98,
1407. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
4. For some recent works in this ®eld, see: (a) Allin, S. M.; Button, M. A. C.; Baird, R. D. Synlett 1998, 1117.
(b) Marcotte, S.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. J. Org. Chem. 1999, 64, 8461. (c) Poerwono, H.;
Higashiyama, K.; Takahashi, H. J. Org. Chem. 1998, 63, 2711. (d) Delorme, D.; Berthelette, C.; Lavoie, R.;
Roberts, E. Tetrahedron: Asymmetry 1998, 9, 3963. (e) Le Bail, M.; Perard, J.; Aitken, D. J.; Husson, H.-P.
Tetrahedron Lett. 1999, 40, 5309. (f) Yamauchi, T.; Fujikura, H.; Higashiyama, K.; Takahashi, H.; Ohmiya, S.
J. Chem. Soc., Perkin Trans. 1 1999, 2791.
5. For a review, see: Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
6. Agami, C.; Comesse, S.; Kadouri-Puchot, C.; Lusinchi, M. Synlett 1999, 1094.
7. (a) Corriu, R. J. P.; Masse, J.; Samate, D. J. Organomet. Chem. 1975, 93, 71. (b) Corriu, R. J. P.; Guerin, C.;
M'Boula, J. Tetrahedron Lett. 1981, 22, 2985.
8. (a) Ayalon-Chass, D.; Ehlinger, E.; Magnus, P. J. Chem. Soc., Chem. Commun. 1977, 772. (b) Ehlinger, E.;
Magnus, P. Tetrahedron Lett. 1980, 11. (c) Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1980, 102, 5004.
9. Amouroux, R.; Chan, T. H. Tetrahedron Lett. 1978, 4453. Lau, P. W. K.; Chan, T. H. Tetrahedron Lett. 1978,
2383.
10. A reaction between this anion and a chiral imine has already been described: Hashimoto, Y.; Takaoti, K.; Sudo,
A.; Ogasawara, T.; Saigo, K. Chem. Lett. 1995, 235.
11. Representative experimental procedure: To a solution of unsaturated silyl derivative (4.4 mmol) and TMEDA (4.4
mmol) in freshly distilled and degassed THF (9 ml) was added, at ^78ꢁC, sec-BuLi (4.4 mmol). The solution was
stirred at ^78ꢁC for 15 min and then warmed to rt for 30 min. After this time, the mixture was cooled to ^78ꢁC and
a solution of oxazolidine (0.88 mmol) in THF (4 ml) was slowly added. After 30 min at ^78ꢁC, the mixture was
allowed to warm to 0ꢁC and was then hydrolyzed. The crude mixture was analyzed by H NMR and puri®ed by
1
chromatography on silica gel (petroleum ether:ethyl acetate, 85:15) to aord the b-amino alcohols 4a±c.
12. The above representative experimental procedure was used but Ti(Oi-Pr)4 (0.88 mmol) was added at ^78ꢁC to the
organolithium reagent mixture and this solution was stirred for 1 h before the addition of the oxazolidine.
13. Yamamoto, H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford,
1991; Vol. 2, pp. 81±97, and references cited therein.
14. Yamamoto, Y. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford,
1991; Vol. 2, pp. 57±60, and references cited therein.
15. Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 2582.
16. Reetz, M. T. In Organotitanium Reagents in Organic Synthesis; Hafner, K.; Rees, C. W.; Trost, B. M.; Lehn, J.-
M.; von Rague Schleyer, P.; Zahradnik, R., Eds. Springer-Verlag: Berlin Heidelberg, 1986; Vol. 24, pp. 123±193.