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For an isolated example where the three stereogenic centers are controled by the chiral ligand L1 see:(d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
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(c) For an isolated example where the three stereogenic centers are controled by the chiral ligand L1 see:(d) Arnold, L. A.; Naasz, R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2001, 123, 5841.
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A portion of these studies have been previously communicated, see:(a) González-Gómez, J. C.; Foubelo, F.; Yus, M. Tetrahedron Lett. 2008, 49, 2343.
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A portion of these studies have been previously communicated, see:(a) González-Gómez, J. C.; Foubelo, F.; Yus, M. Tetrahedron Lett. 2008, 49, 2343.
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(b) Highlights: Synfacts 2008, 7. 0725.
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0033582571
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N-tertButanesulfinyl imines are readily prepared from aldehydes and N-tertbutanesulfinamides (Ss and Rs are commercially available in >99% ee), following the procedure reported in: Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
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N-tertButanesulfinyl imines are readily prepared from aldehydes and N-tertbutanesulfinamides (Ss and Rs are commercially available in >99% ee), following the procedure reported in: Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
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In the aziridination of sulfinimines it was recognized early that the replacement of the p-toluene motif with a tert-butyl group significantly increased the stereoinduction: García Ruano, J. L.; Fernandez, I.; Hamdouchi, C. Tetrahedron Lett. 1995, 36, 295.
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For an example where a chiral acetal overcome the directing induction of the chiral enolate in a tandem enantioselective conjugate addition-aldol reaction, see:(a) Alexakis, A.; Trevitt, G. P.; Bernardinelli, G. J. Am. Chem. Soc. 2001, 123, 4358.
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34247582194
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To the best of our knowledge, only a few examples of multicomponent reactions Mat include chiral sulfinimines have been recently reported:(a) Kamimura, A.; Okawa, H.; Morisaki, Y.; Ishikawa, S.; Uno, H. J. Org. Chem. 2007, 72, 3569.
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The scope of the reaction was studied using 0.5 mmol of sulfinimines and 1.5 equiv of enone. However, compounds 3h and 3q were prepared using 1.2 equiv of enone, on a 2 mmol scale, observing similar isolated yields and stereoselectivities.
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The scope of the reaction was studied using 0.5 mmol of sulfinimines and 1.5 equiv of enone. However, compounds 3h and 3q were prepared using 1.2 equiv of enone, on a 2 mmol scale, observing similar isolated yields and stereoselectivities.
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4644252638
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Crystal data (excluding structure factors) deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 671456.
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Crystal data (excluding structure factors) deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 671456.
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