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4.5. Slow addition of achiral base
Lett. 1995, 36, 2847±2850. &e) Asami, M.; Inoue, S.
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1996, 7, 407±408. &h) Khan, A. Z.-Q.; de Groot, R. W.;
The diamine 2 &16 mmol, 0.05 equiv.), DBU [either
10 equiv. &3.1 mmol) or 0 equiv.], and cyclohexene oxide
&0.31 mmol) was dissolved in THF &containing ca. 10 mg
n-dodecane as internal standard for GC analysis). The
amount of THF was either 2.0 mL &when using 10 equiv.
DBU) or 2.5 mL &0 equiv. DBU). LDA &0.47 mmol) was
then added to the reaction mixture at 08C either during
5 min or 5 h &syringe pump). After stirring at 08C for a
total of 16 h, the reaction mixture was diluted with Et2O
&15 mL) and washed with 10% aqueous citric acid
&2£5 mL), water &5 mL), and brine &5 mL) and dried
&MgSO4). Conversion and enantiomeric excess were
determined by chiral GC &Chirasil Dex-CB column).
È
Arvidsson, P. I.; Davidsson, O. Tetrahedron: Asymmetry
1998, 9, 1223±1229. &i) O'Brien, P.; Poumellec, P. J. Chem.
Soc., Perkin Trans. 1 1998, 2435±2441. &j) O'Brien, P.;
Towers, T. D.; Voith, M. Tetrahedron Lett. 1998, 39, 8175±
8178. &k) de Sousa, S. E.; O'Brien, P.; Steffens, H. C.
Tetrahedron Lett. 1999, 40, 8423±8425. &l) O'Brien, P.;
Pilgram, C. D. Tetrahedron Lett. 1999, 40, 8427±8430.
&m) Colman, B.; de Sousa, S. E.; O'Brien, P.; Towers, T. D.;
Watson, W. Tetrahedron: Asymmetry 1999, 10, 4175±4182.
&n) Asami, M.; Ogawa, M.; Inoue, S. Tetrahedron Lett. 1999,
40, 1563±1564. &o) Kee, A.; O'Brien, P.; Pilgram, C. D.;
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Tetrahedron 2000, 56, 9633±9640.
Acknowledgements
This work was supported by the Swedish Natural Research
Council &NFR), the Swedish Research Council for
Engineering Sciences &T. F. R.), and the Swedish Council
for Strategic Research &S. S. F.). We are grateful to Dr
È
Mikael J. Sodergren for valuable help with the manuscript
preparation.
8. Asami, M.; Suga, T.; Honda, K.; Inoue, S. Tetrahedron Lett.
1997, 38, 6425±6428.
È
9. &a) Sodergren, M. J.; Andersson, P. G. J. Am. Chem. Soc. 1998,
120, 10760±10761. &b) Sodergren, M. J.; Bertilsson, S. K.;
È
Andersson, P. G. J. Am. Chem. Soc. 2000, 122, 6610±6618.
È
10. Bertilsson, S. K.; Sodergren, M. J.; Andersson, P. G. J. Org.
Chem.. 2002, 67, 1567±1573.
11. LDA alone reacts slowly with cyclohexene oxide under the
applied reaction conditions resulting in conversions of about
5% after 2 h. See Ref. 9.
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