Matthias Eggenstein, Anika Thomas, J. Theuerkauf
Mar 1, 2009
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Advanced Synthesis & Catalysis
Abstract
A set of novel phosphine-phosphorami- dite ligands possessing two elements of chirality have been prepared through a modular synthetic approach. The ligands (11bS)-N-(2-(diphenylphos- phino)phenyl)-N-((S)-1-phenylethyl)dinaphtho(2,1- d:1',2'-f)Aphepin-4-amine ((Sa,Sc)-1a) and (11bR)-N-(2-(diphenylphosphino)phenyl)-N- ((S)-1-(1-naphthyl)ethyl)dinaphtho(2,1-d:1',2'-f)- Aphepin-4-amine ((Sa,Sc)-1b) are unique in providing enantioselectivities 96% ee and 94% ee, respectively, in mechanistically dis- tinct hydrogenations of C=C, C= Na nd C=O double bonds in combination with three different transition metals (rhodium, iridium, and ruthenium, respec- tively). Particularly remarkable are the enantiomer- ic excesses up to 97% achieved in the iridium-cata- lyzed hydrogenation of 2-substituted quinolines, where (11bS)-N-(2-(diphenylphosphino)phenyl)-N-