Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs

Carolyn E. Anderson, Yariv Donde, Christopher J. Douglas, Larry E. Overman

Research output: Contribution to journalArticlepeer-review

119 Scopus citations

Abstract

(Chemical Equation Presented) Palladium(II) catalysts based on a ferrocenyloxazoline palladacyclic (FOP) scaffold were synthesized and evaluated for the rearrangement of prochiral allylic N-(4-methoxyphenyl)benzimidates. When iodide-bridged dimer FOP precatalysts are activated by reaction with excess silver trifluoroacetate, the allylic rearrangement of both E and Z prochiral primary allylic N-(4-methoxyphenyl)-benzimidates takes place at room temperature to give the corresponding chiral allylic N-(4-methoxyphenyl)benzamides in high yield and good ee (typically 81-95%). Several allylic imidate motifs were evaluated also. Because the corresponding enantioenriched allylic amide products can be deprotected in good yield to give enantioenriched allylic amines, allylic N-aryltrifiuoroacetimidates were identified as promising substrates.

Original languageEnglish (US)
Pages (from-to)648-657
Number of pages10
JournalJournal of Organic Chemistry
Volume70
Issue number2
DOIs
StatePublished - Jan 21 2005

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