Journal
ORGANIC LETTERS
Volume 21, Issue 4, Pages 984-988Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b03959
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Funding
- National Institutes of Health [GM-128695]
- Boston College
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An efficient method for the coupling of N-alkylamines with silicon enolates to generate beta-amino carbonyl compounds is disclosed. These reactions proceed by activation of alpha-amino C-H bonds by B(C6F5)(3), which likely generates a frustrated acid/base complex in the presence of large N-alkylamines. The transformation requires no external oxidant and releases hydrosilane as a byproduct. The utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetine.
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