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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Synthesis of 1- and 1,2-Substituted Cyclopropylamines from Ketone Homoenolates
Michael S West1, Julia E Pia1, Sophie A L Rousseaux1
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Abstract:
Ketone homoenolates are intermediates with both nucleophilic and electrophilic properties. While there are several reports on their use as nucleophiles, there are few reports on their potential as electrophiles. Herein, we report the use of ketone zinc/copper homoenolates as electrophiles in the synthesis of 1- and 1,2-substituted cyclopropylamines. We found that CuCN·2LiCl is essential to produce a more reactive homoenolate intermediate. We also report a facile telescoped sequence from β-substituted enones toward 1,2-disubstituted cyclopropylamines.
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