A supramolecularly tunable chiral diphosphine ligand: application to Rh and Ir-catalyzed enantioselective hydrogenation

Chemical Science
Xi-Chang ZhangWenjun Fang

Abstract

A supramolecularly tunable chiral bisphosphine ligand bearing two pyridyl-containing crown ethers, (-) or (+)-Xyl-P16C6-Phos, was fabricated and utilized in the Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid esters and Ir-catalyzed asymmetric hydrogenation of quinolines in high yields with excellent enantioselectivities (90-99% ee). Up to a 22% enhancement in enantioselectivity was achieved by the addition of certain amounts of alkali ions (Li+, Na+ or K+), which could be selectively recognized and effectively complexed by the crown ethers on the chiral Xyl-P16C6-Phos.

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Citations

Aug 23, 2016·Chemical Communications : Chem Comm·Mónica VaqueroAnton Vidal-Ferran
Jan 27, 2019·Chemical Communications : Chem Comm·Yan LiLaurent Bouteiller
Jan 28, 2021·Chemical Society Reviews·Jonathan Trouvé, Rafael Gramage-Doria
May 21, 2020·Journal of the American Chemical Society·Tao HongPeter J Stang

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Methods Mentioned

BETA
NMR

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