Journal
ORGANIC LETTERS
Volume 24, Issue 32, Pages 5869-5873Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01634
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Funding
- NSERC
- Canada Foundation for Innovation [35261, 19119]
- Government of Ontario (Ontario Research Fund and Early Researcher Award)
- Alfred P. Sloan Foundation
- University of Toronto
- Ontario Research Fund
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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.
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.
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