Abstract
Cyclohexene N-p-toluenesulfonylimine (1) undergoes enantioselective ring opening to 2b upon treatment with methylmagnesium halides or MeLi in the presence of chiral Cu-catalysts. No activation of the aziridine by Lewis acid is required. Enantioselectivities of up to 91% have been observed under optimized conditions with the chiral imine ligand derived from phenylalanine. The same system reacts with cyclohexene oxide to afford trans-2-methylcyclohexanol with 50% yield and 10% ee.
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