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

06 September 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

cyclopropylamine
zinc homoenolate
α-chloroaldehyde

Supplementary materials

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Title
Rousseaux - Cyclopropylamines - SI ChemRxiv
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