Synthesis of 1-and 1,2-Substituted Cyclopropylamines from Ketone Homoenolates

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 beta-substituted enones toward 1,2-disubstituted cyclopropylamines.

Automated summary

This study reports the use of ketone zinc/copper homoenolates as electrophiles in the synthesis of 1-and 1,2-substituted cyclopropylamines. CuCN.2LiCl is found to be essential in producing a more reactive homoenolate intermediate. Additionally, a facile telescoped sequence from beta-substituted enones towards 1,2-disubstituted cyclopropylamines is presented.