An article Synthesis of trans-2-Substituted Cyclopropylamines from alpha-Chloroaldehydes WOS:000492114600055 published article about NUCLEOPHILIC CYCLOPROPANATION; ASYMMETRIC CYCLOPROPANATION; 3+2 ANNULATION; AMINO-ACIDS; C-C; BIS(IODOZINCIO)METHANE; AMINOCYCLOPROPANES; CYCLOADDITION; 1,4-ADDITION; HOMOENOLATE in [West, Michael S.; Mills, L. Reginald; McDonald, Tyler R.; Lee, Jessica B.; Ensan, Deeba; Rousseaux, Sophie A. L.] Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada; [Lee, Jessica B.] Paraza Pharma Inc, 275 Blvd Armand Frappier, Laval, PQ H7V 4A7, Canada; [Ensan, Deeba] Ontario Inst Canc Res, 661 Univ Ave Suite 510, Toronto, ON M5G 0A3, Canada in 2019, Cited 48. The Name is 1,4-Dioxa-8-azaspiro[4.5]decane. Through research, I have a further understanding and discovery of 177-11-7. Computed Properties of C7H13NO2
Cyclopropylamines are prevalent in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available alpha-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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