1 research outputs found
Enantioselective Copper-Catalyzed Borylative Amidation of Allenes
An
approach for the copper-catalyzed synthesis of enantioenriched
amides bearing an α-stereogenic center is disclosed. This method
involves the addition of an allyl copper species to an isocyanate
and allows access to α-substituted chiral amides in high yields
and high-to-excellent enantioselectivities. The utility of α-vinyl
β-boryl amides in synthesis is highlighted by the diversification
of products to afford highly useful scaffolds. DFT calculations reveal
that the catalyst preferentially coordinates to the oxygen of the
isocyanate. Enantiocontrol arises from the steric repulsion between
the boryl group and the stereodirecting phenyl of the chiral ligand