Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates

Qi Zhang, David P. Stockdale, Jason C. Mixdorf, Joseph J. Topczewski, Hien M. Nguyen

Research output: Contribution to journalArticlepeer-review

52 Scopus citations

Abstract

The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetimidates with Et3N·3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles with Et3N·3HF using a chiral-diene-ligated Ir complex. The methodology enables the formation of acyclic fluorine-containing compounds in good yields with excellent levels of asymmetric induction and overcomes the limitations previously associated with the enantioselective construction of secondary allylic fluorides bearing α-linear substituents.

Original languageEnglish (US)
Pages (from-to)11912-11915
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number37
DOIs
StatePublished - Sep 23 2015

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© 2015 American Chemical Society.

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