69048-31-3Relevant academic research and scientific papers
Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines
Wakchaure, Vijay N.,Kaib, Philip S. J.,Leutzsch, Markus,List, Benjamin
supporting information, p. 11852 - 11856 (2015/10/05)
A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross-coupling of ketones with diverse amines, and it was applied in the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline. A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O was developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method was successfully applied to the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline.
Fast racemisation of chiral amines and alcohols by using cationic half-sandwich ruthena- and iridacycle catalysts
Jerphagnon, Thomas,Gayet, Arnaud J.A.,Berthiol, Florian,Ritleng, Vincent,Mrsic, Natasa,Meetsma, Auke,Pfeffer, Michel,Minnaard, Adriaan J.,Feringa, Ben L.,De Vries, Johannes G.
experimental part, p. 12780 - 12790 (2010/06/16)
The lipase-catalysed resolution of alcohols and amines yields only 50% of the desired enantiopure product. However, addition of a racemisation catalyst leads to 100% yield in what is called a dynamic kinetic resolution (DKR). There is a need for new racemisation catalysts that are fast and compatible with the conditions of the enzymatic reaction. We show that cationic half-sandwich ruthena- and iridacycle complexes are highly active and efficient in the racemisation of chiral alcohols and amines. Upon activation with base, these complexes are able to selectively racemise alcohols, whereas the non-activated complexes are selective catalysts for the racemisation of amines. We have applied the iridacycles in the DKR of racemic β-chloroalcohols to produce chiral epoxides in a biphasic system in good yields and high ee (ee = enantiomeric excess).
Local and tunable n→π* interactions regulate amide isomerism in the peptoid backbone
Gorske, Benjamin C.,Bastian, Brent L.,Geske, Grant D.,Blackwell, Helen E.
, p. 8928 - 8929 (2008/02/09)
We report that n→π* interactions are operative in peptoids and play a major role in controlling amide isomerism. These interactions can be tuned using α-chiral amide side chains known to promote peptoid folding. To our knowledge, this is the first report of n→π* interactions between amides in non-prolyl systems. Furthermore, we have characterized an n→π* interaction between backbone carbonyls and side chain aromatic rings that can dramatically stabilize the cis-amides required for peptoid helix formation. The tunability of both types of n→π* interactions in peptoids has significant implications for peptoid folding and could be exploited for the design of new peptoid architectures. Copyright
