1091606-74-4Relevant academic research and scientific papers
The asymmetric aza-claisen rearrangement: development of widely applicable pentaphenylferrocenyl palladacycle catalysts
Fischer, Daniel F.,Barakat, Assem,Xin, Zhuo-Qun,Weiss, Matthias E.,Peters, Rene
supporting information; experimental part, p. 8722 - 8741 (2010/03/31)
Systematic studies have been performed to develop highly efficient catalysts for the asymmetric aza-Claisen rearrangement of trihaloacetimidates. Herein, we describe the stepwise development of these catalyst systems involving four different catalyst generations finally resulting in the development of a planar chiral pentaphenylferrocenyl oxazoline palladacycle. This complex is more reactive and has a broader substrate tolerance than all previously known catalyst systems for asymmetric aza-Claisen rearrange-ments. Our investigations also reveal that subtle changes can have a big impact on the activity. With the enhanced catalyst activity, the asymmetric aza-Claisen rearrangement has a very broad scope: the methodology not only allows the formation of highly enantioenriched primary allylic amines, but also secondary and tertiary amines; al-lylic amines with N-substituted quaternary stereocenters are conveniently accessible as well. The reaction conditions tolerate many important functional groups, thus providing stereoselective access to valuable functionalized building blocks, for example, for the synthesis of unnatural amino acids. Our results suggest that face-selective olefin coordination is the enantioselectivitydetermining step, which is almost exclusively controlled by the element of planar chirality.
METHOD FOR THE PREPARATION OF AMINOPHOSPHINE LIGANDS AND THEIR USE IN METAL CATALYSTS
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Page/Page column 52-53, (2009/01/24)
The present application is directed to i) a two-step method for synthesizing phosphme-ammophosphme (P,N,P) ligands, ii) the use of such ligands in the preparation of metal complexes as hydrogenation catalysts, and iii) ammophosphme (P,N) and phosphme-ammo
Preparation and diastereoselective ortho-metalation of chiral ferrocenyl imidazolines: Remarkable influence of LDA as metalation additive
Peters, Rene,Fischer, Daniel F.
, p. 4137 - 4140 (2007/10/03)
(Chemical Equation Presented) The preparation of optically pure ferrocenyl imidazolines starting from ferrocenecarboxylic acid and the application to diastereoselective ortho-metalations is described highlighting the remarkable influence of lithium dialky
Fluorine for hydroxy substitution in biogenic amines: Asymmetric synthesis and biological evaluation of fluorine-18-labeled β-fluorophenylalkylamines as model systems
Van Dort,Jung,Sherman,Kilbourn,Wieland
, p. 810 - 815 (2007/10/02)
This work explores the biomimetic potential of [18F]fluorine for hydroxy substitution in β-phenethanolamines as a possible strategy for developing radiotracers for in vivo imaging. Stereospecific syntheses of the two model compounds (1R,2S)-1-[
Optically pure chiral sulfoxides using ephedrine as a chiral auxiliary
Benson, Scott C.,Snyder, John K.
, p. 5885 - 5888 (2007/10/02)
Optically pure chiral sulfoxides can be formed in good to excellent yields by sequential displacement reactions of organometallic reagents on the 1,2,3-oxathiazolidine-S-oxide formed from ephedrine and thionyl chloride, a modification of the Wudl and Lee procedure.
