372199-89-8Relevant 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.
Synthesis of α-amido ketones via organic catalysis: Thiazolium-catalyzed cross-coupling of aldehydes with acylimines [12]
Murry,Frantz,Soheili,Tillyer,Grabowski,Reider
, p. 9696 - 9697 (2007/10/03)
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