913974-39-7Relevant academic research and scientific papers
Macrocyclic ferrocenyl-bisimidazoline palladacycle dimers as highly active and enantioselective catalysts for the Aza-Claisen rearrangement of Z-configured N-para-methoxyphenyl trifluoroacetimidates
Jautze, Sascha,Seiler, Paul,Peters, Rene
, p. 1260 - 1264 (2008/03/27)
(Chemical Equation Presented) In just four steps from ferrocene, macrocyclic ferrocenyl bispalladacyles have been synthesized by using a diastereoselective biscyclopalladation reaction as the key step. The complexes not only possess a fascinating structur
Practical, highly active, and enantioselective ferrocenyl-imidazoline palladacycle catalysts (FIPs) for the aza-claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates
Weiss, Matthias E.,Fischer, Daniel F.,Xin, Zhuo-Qun,Jautze, Sascha,Schweizer, W. Bernd,Peters, Rene
, p. 5694 - 5698 (2008/02/04)
Just a pinch of catalyst: Just 0.05 mol % of a novel planar chiral ferrocenyl-imidazoline palladacycle catalyst (FIP) is sufficient to catalyze a highly efficient aza-Claisen rearrangement of N-para-methoxyphenyl trifluoroacetimidates and thereby provide access to chiral protected primary allylic amines with unprecedentedly high enantioselectivities (see scheme). (Chemical Equation Presented).
Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs
Anderson, Carolyn E.,Donde, Yariv,Douglas, Christopher J.,Overman, Larry E.
, p. 648 - 657 (2007/10/03)
(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.
