Tetrahedron

ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction

…, C Papamicaël, G Dupas, F Marsais, V Levacher

Index: Gaillard, Stephane; Papamicael, Cyril; Dupas, Georges; Marsais, Francis; Levacher, Vincent Tetrahedron, 2005 , vol. 61, # 34 p. 8138 - 8147

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Citation Number: 25

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 ...