84993-37-3Relevant articles and documents
Enantioselective Synthesis of α-Amidoboronates Catalyzed by Planar-Chiral NHC-Cu(I) Complexes
Schwamb, C. Benjamin,Fitzpatrick, Keegan P.,Brueckner, Alexander C.,Richardson, H. Camille,Cheong, Paul H.-Y.,Scheidt, Karl A.
supporting information, p. 10644 - 10648 (2018/09/06)
The first highly selective catalytic hydroboration of alkyl-substituted aldimines to provide medicinally relevant α-amidoboronates is disclosed. The Cu(I)-catalyzed borylation proceeds with excellent facial selectivity when a set of planar-chiral N-heterocyclic carbenes (NHCs) were employed as ligands. Density functional theory computations suggest that interactions between BPin and the planar-chiral catalyst are responsible for the observed stereoselectivity. Important pharmacophores, such as the boronate analogue of isoleucine, can be prepared using a chromatography-free protocol starting from commercially available reagents. The application of these NHC ligands in these Cu(I)-catalyzed processes offers a significant contribution to existing strategies for laboratory-scale preparation of enantioenriched α-amidoboronates.
A NEW GENERAL METHOD OF α-AMIDO-ALKYLATION
Morton, J.,Rahim, A.,Walker, E. R. H.
, p. 4123 - 4126 (2007/10/02)
N-(1-p-Toluenesulphonyl-alkyl) amides, which are readily prepared from an aldehyde, an amide and sodium p-toluenesulphinate, are versatile α-amido-alkylating agents for sulphur nitrogen and carbon nucleophiles.
