872357-82-9Relevant academic research and scientific papers
Design, preparation, and implementation of an imidazole-based chiral biaryl P,N-ligand for asymmetric catalysis
Cardoso, Flavio S. P.,Abboud, Khalil A.,Aponick, Aaron
supporting information, p. 14548 - 14551 (2013/10/22)
A new strategy for increasing the barrier to rotation in biaryls has been developed that allows for the incorporation of 5-membered aromatic heterocycles into chiral atropisomers. Using this concept, an imidazole-based biaryl P,N-ligand has been designed and prepared as a single enantiomer. This ligand performs exceptionally well in the enantioselective A3-coupling, demonstrating the potential of this new design element.
Practical highly enantioselective synthesis of propargylamines through a copper-catalyzed one-pot three-component condensation reaction
Gommermann, Nina,Knochel, Paul
, p. 4380 - 4392 (2008/02/07)
The one-pot three-component reaction of terminal alkynes, aldehydes and secondary amines in the presence of copper(1) bromide/quinap is reported. The reaction scope has been determined and a broad variety of all three components has been used, which afforded the corresponding propargylamines in good to excellent yields and moderate to very good enantioselectivities. The reaction showed a strong positive nonlinear effect. The transformation of a propargylamine intermediate into the alkaloid (S-(+)-coniine has also been described.
Preparation of functionalized primary chiral amines and amides via an enantioselective three-component synthesis of propargylamines
Gommermann, Nina,Knochel, Paul
, p. 11418 - 11426 (2007/10/03)
A general preparation of functionalized primary chiral amines and amides from propargylamines has been developed. The chirality is established by an enantioselective three-component reaction of an aldehyde, a terminal alkyne and a secondary amine in the p
Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesis of (S)-(+)-coniine
Gommermann, Nina,Knochel, Paul
, p. 2324 - 2325 (2007/10/03)
The one-pot three-component addition reaction of trimethylsilylacetylene, aldehydes and dibenzylamine provides in the presence of CuBr/Quinap as catalyst, various enantiomerically enriched propargylamines in good yields (up to 99%) and excellent enantiomeric excess (up to 98% ee) which can be used as a key intermediate in the synthesis of the alkaloid (S)-(+)-coniine.
