jo048490r_si_001.cif (16.34 kB)
Catalytic Asymmetric Synthesis of Chiral Allylic Amines. Evaluation of Ferrocenyloxazoline Palladacycle Catalysts and Imidate Motifs
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posted on 2005-01-21, 00:00 authored by Carolyn E. Anderson, Yariv Donde, Christopher J. Douglas, Larry E. OvermanPalladium(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-aryltrifluoroacetimidates
were identified as promising substrates.
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allylic imidate motifsallylic rearrangementferrocenyloxazoline palladacyclicmethoxyphenylFerrocenyloxazoline Palladacycle CatalystsZ prochiralallylic NCatalytic Asymmetric SynthesisFOPenantioenriched allylic amide productsenantioenriched allylic aminesChiral Allylic Aminessilver trifluoroacetateroom temperature
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