Abstract
Treatment of sulfinylaziridines, which were synthesized from 1-chloroalkyl p-tolyl sulfoxides and imines, with ethylmagnesium bromide gave nonstabilized aziridinylmagnesiums by a sulfoxide-magnesium exchange reaction. The cross-coupling of the aziridinylmagnesiums with various kinds of alkylhalides was realized in high yields by using Cu(I) iodide as a catalyst, and the reaction was found to be stereospecific. The coupling products were hydrogenated with Pd(OH) 2 in alcohol to give the amines bearing a quaternary chiral center in quantitative yields. Synthesis of both enantiomers of the amines bearing a quaternary chiral center was realized starting from optically active ( R)-chloromethyl p-tolyl sulfoxide in good overall yields with perfect asymmetric induction.
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