1174154-30-3Relevant academic research and scientific papers
Kinetic resolution of unsaturated amides in a chlorocyclization reaction: Concomitant enantiomer differentiation and face selective alkene chlorination by a single catalyst
Jaganathan, Arvind,Staples, Richard J.,Borhan, Babak
supporting information, p. 14806 - 14813 (2013/10/22)
The first example of a kinetic resolution via chlorofunctionalization of olefins is reported. The enantiomers of racemic unsaturated amides were found to have different hydrogen-bonding affinities for chiral Lewis bases in numerous solvents. This interaction was exploited in developing a kinetic resolution of racemic unsaturated amides via halocyclization. The same catalyst serves to both sense chirality in the substrate as well as mediate a highly face-selective chlorine delivery onto the olefin functionality, resulting in stereotriad products in up to 99:1 dr and up to 98.5:1.5 er. The selectivity factors were typically greater than 50 to allow for the simultaneous synthesis of both the products and unreacted substrates in highly enantioenriched form at yields approaching 50%. The reaction employs catalytic amounts (≤0.50 mol %) of a commercially available and recyclable organocatalyst.
A dual-catalysis/anion-binding approach to the kinetic resolution of allylic amines
Klauber, Eric G.,Mittal, Nisha,Shah, Tejas K.,Seidel, Daniel
, p. 2464 - 2467 (2011/07/09)
Chemical equations presented. A dual-catalysis approach enables the small-molecule catalyzed kinetic resolution of allylic amines by acylation. By employing 2 mol % of each 4-(pyrrolidino)pyridine (PPY) and a readily available chiral hydrogen-bonding coca
Asymmetric synthesis of 4H-1,3-oxazines: Enantioselective reductive cyclization of N-acylated β-amino enones with trichlorosilane catalyzed by chiral Lewis bases
Sugiura, Masaharu,Kumahara, Mako,Nakajima, Makoto
supporting information; experimental part, p. 3585 - 3587 (2009/12/03)
N-Acylated β-amino enones reductively cyclize by treatment with trichlorosilane and a chiral Lewis base catalyst to afford optically active 4H-1,3-oxazines, which can be transformed to other chiral compounds without racemization.
