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Synthesis of trans-2-Substituted Cyclopropylamines from α‑Chloroaldehydes

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journal contribution
posted on 07.10.2019 by Michael S. West, L. Reginald Mills, Tyler R. McDonald, Jessica B. Lee, Deeba Ensan, Sophie A. L. Rousseaux
Cyclopropylamines are prevalent in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring closure to generate the cyclopropylamine. We have also observed that cyclopropylamine cis/trans-isomerization occurs in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic cosolvent.