Direct Regioselective γ-Amination of Enones
Xiaohong Chen1, Xiaoguang Liu1, Justin T Mohr1
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.
Organic Letters
|February 4, 2016
Summary
Researchers achieved regioselective C-N bond formation in carbonyl compounds using enone substrates and azodicarboxylate electrophiles. This controlled amination reaction is stereoselective and works with sterically demanding nucleophiles.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
Background:
- Carbonyl compounds with a gamma-amino group are important in medicinal chemistry.
- Developing efficient synthetic routes to these compounds is crucial.
Purpose of the Study:
- To achieve regioselective gamma-C-N bond formation in simple enone substrates.
- To explore a novel amination strategy using azodicarboxylate electrophiles.
Main Methods:
- Utilized controlled dienolate reactivity of enone substrates.
- Employed azodicarboxylate electrophiles for amination.
- Investigated reactions with sterically demanding nucleophiles.
Main Results:
- Achieved regioselective gamma-C-N bond formation.
- Demonstrated the reaction's efficacy with sterically hindered nucleophiles.
- Observed stereoselective outcomes in the amination process.
Conclusions:
- Developed a facile method for synthesizing gamma-amino carbonyl compounds.
- The controlled dienolate reactivity offers a versatile approach to C-N bond formation.
- The stereoselective amination is valuable for pharmaceutical development.
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