Synthesis of Stereodefined Cyclopropylamine Derivatives from Cyclopropanols and Sulfinamides

The synthesis of cyclopropylamine derivatives has been achieved by the reaction of a cyclopropanol and a sulfinamide in the presence of base and a Zn(II) salt via a ring-opened homoenolate intermediate. Enantioenriched cyclopropylamines are accessible by chiral resolution using enantioenriched sulfinamide nucleophiles. These sulfinamide products can be derivatized to unprotected cyclopropylamines or oxidized to various S(VI) functional groups, providing easy access to stereodefined cyclopropylamine derivatives (up to >20:1 dr and >99% ee).