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

preprint
submitted on 04.09.2019, 00:24 and posted on 06.09.2019, 02:05 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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