Synthesis of Imidates: TFA-Mediated Regioselective Amide Alkylation Using Meerwein's Reagent

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Abstract

Regioselective O-alkylation of an amide to form the corresponding imidate is a common synthetic problem, often resulting in varying amounts of N-alkylation. Screening existing methods for converting amides to imidates gave inconsistent or irreproducible results, sometimes affording N-alkylamide as the major product. A simple and reliable protocol for amide O-alkylation with complete regioselectivity has been designed, and its scope and efficiency demonstrated on a number of substrates.

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  • Organic Chemistry
Original languageEnglish
Pages (from-to)3470-3472
Number of pages3
JournalJournal of Organic Chemistry
Volume81
Issue number8
Publication statusPublished - 2016 Apr 15
Publication categoryResearch
Peer-reviewedYes