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

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...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 20; pp. 8409 - 8413
Main Authors West, Michael S, Mills, L. Reginald, McDonald, Tyler R, Lee, Jessica B, Ensan, Deeba, Rousseaux, Sophie A. L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.10.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HOMOENOLATE
3+2 ANNULATION
CYCLOADDITION
BIS(IODOZINCIO)METHANE
AMINO-ACIDS
ASYMMETRIC CYCLOPROPANATION
NUCLEOPHILIC CYCLOPROPANATION
C-C
AMINOCYCLOPROPANES
1,4-ADDITION
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03172