654679-08-0Relevant academic research and scientific papers
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.
Enantioselective synthesis of chiral α-aminoalkyl-1,2,3-triazoles using a three-component reaction
Gommermann, Nina,Gehrig, Anna,Knochel, Paul
, p. 2796 - 2798 (2007/10/03)
A range of chiral α-aminoalkyl-1,2,3-triazoles have been prepared in a modular fashion in 3 steps with up to 98% ee. The key step is a CuBr/Quinap-catalyzed enantioselective asymmetric three-component synthesis of propargylamines. Georg Thieme Verlag Stut
Synthesis of chiral α-aminoalkylpyrimidines using an enantioselective three-component reaction
Dube, Henry,Gommermann, Nina,Knochel, Paul
, p. 2015 - 2025 (2007/10/03)
A range of chiral α-aminoalkylpyrimidines has been prepared in a modular fashion in 5 steps with up to 98% ee. The key step is a CuBr-catalyzed enantioselective asymmetric three-component synthesis of propargylic amines.
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.
Readily available biaryl P,N ligands for asymmetric catalysis
Knoepfel, Thomas F.,Aschwanden, Patrick,Ichikawa, Takashi,Watanabe, Takumi,Carreira, Erick M.
, p. 5971 - 5973 (2007/10/03)
A short and modular synthesis of novel P,N ligands (pinap; see scheme; X = O or NH) is presented. A covalently bound chiral group allows the separation of the atropisomeric diastereomers, thus avoiding resolution involving chiral Pd-amine complexes. The utility of the ligands is demonstrated for three reactions catalyzed by different transition metals; in each case products are obtained with high enantiomeric excess (up to 99% ee).
