Journal
ORGANIC LETTERS
Volume 14, Issue 17, Pages 4686-4689Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol302180v
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- Aix-Marseille Universite
- CNRS
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Direct alpha-arylation reactions of secondary beta-keto amides with arynes, generated by fluoride-induced elimination of ortho-silyl aryltriflates, are described. The transformation proceeds via an interrupted insertion reaction of arynes and leads to densely functionalized aromatic compounds exhibiting a chiral 'all carbon' quaternary center under transition-metal-free conditions. An organocatalytic asymmetric version of the reaction also proved possible, affording the proof of concept that arynes can be involved in enantioselective transformations.
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