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Synthesis of Trans-2-Substituted-Cyclopropylamines from α-Chloroaldehydes

preprint
submitted on 04.09.2019 and posted on 06.09.2019 by Michael West, L. Reginald Mills, Tyler McDonald, Jessica Lee, Deeba Ensan, Sophie Rousseaux

Cyclopropylamines are prevalent motifs 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 product. We have also observed that cis/trans-isomerization of the cyclopropylamine can occur in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic co-solvent to the reaction.

History

Email Address of Submitting Author

sophie.rousseaux@utoronto.ca

Institution

University of Toronto

Country

Canada

ORCID For Submitting Author

0000-0002-6505-5593

Declaration of Conflict of Interest

no conflict of interest

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