ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction |
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Authors: | Stéphane Gaillard Georges Dupas Francis Marsais Vincent Levacher |
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Institution: | Laboratoire de Chimie Organique Fine et Hétérocyclique UMR 6014 IRCOF, CNRS, Université et INSA de Rouen, BP 08, 76131 Mont-Saint-Aignan Cédex, France |
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Abstract: | The sulfoximine group proved to be an excellent ortho-directing group in lithiation reactions. Several electrophiles were used to afford the corresponding ortho-functionalized aryl sulfoximines in good yields. The use of prochiral electrophiles lead to modest to good diastereoselectivities up to 95%. During this study, we observed a side reaction due to a S-de-tert-butylation. After optimization of this S-de-tert-butylation reaction, the corresponding enantiopure sulfinamides could be obtained in good yields. |
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Keywords: | Sulfoximine Lithiation Sulfinamide Asymmetric synthesis |
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