The development of
novel ligands specifically tailored for homogeneous
gold catalysis is essential for a new generation of gold catalysis.
In this work, we report the development of remotely functionalized
biphenyl-2-ylphosphine ligands based on strategic positioning in cationic
gold catalysts of frustrated Lewis pairs (FLP), that is, basic tertiary
amine moieties and the acidic gold center. By rationally tuning the
location and size of the basic group, these Lewis pairs exhibit little
or modest quenching and importantly enable regiodivergent and stereoselective
isomerizations of propargylic esters into synthetically versatile
dienyl esters under exceptionally mild conditions. Notably, the implementation
of the concept of FLP in gold catalysis is rare.
A highly efficient strategy for the kinetic resolution of axially chiral BINAM derivatives involving a chiral Brønsted acid-catalyzed imine formation and transfer hydrogenation cascade process was developed. The kinetic resolution provides a convenient route to chiral BINAM derivatives in high yields with excellent enantioselectivities.
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