200135-59-7Relevant academic research and scientific papers
Structure and Reactivity of a Sulfoximine-Stabilized Chiral Dilithiocarbanion
Mueller, Juergen F. K.,Neuburger, Markus,Zehnder, Margareta
, p. 2182 - 2190 (1997)
The synthesis and X-ray analysis of a racemic dilithiated S-ethyl-N-methyl-S-phenylsulfoximine cluster 2 with N,N,N',N'-tetramethylethane-1,2-diamine (TMEDA) as coordinating solvent is presented. The lithium complex 2 consists of a mixed tetrameric mono- and dilithio salt. Unexpectedly, a separation of the enantiomers in mono-and dilithiated antipodes with respect to the chirality center on the S-atom is observed. Dilithiation of S-ethyl-N-methyl-S-phenylsulfoximine (1) affords a chiral dinucleophile which undergoes highly regio- and stereoselective alkylation reactions with bis-electrophiles.
Ortho-Lithiation of S-tert-butyl-S-phenylsulfoximines. New route to enantiopure sulfinamides via a de-tert-butylation reaction
Gaillard, Stéphane,Papamica?l, Cyril,Dupas, Georges,Marsais, Francis,Levacher, Vincent
, p. 8138 - 8147 (2007/10/03)
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 mo
