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Palladium-catalyzed asymmetric hydrogenation of lactones under base-free conditions.

ABSTRACT: Asymmetric hydrogenation of esters through homogeneous catalysis is a significantly important transformation in organic synthesis. The systems developed so far mainly focused on chiral iridium and ruthenium catalysts, which required a base to facilitate the activity. Herein, we present a palladium-catalyzed asymmetric hydrogenation of lactones under base-free conditions through dynamic kinetic resolution and kinetic resolution. The reaction exhibits high enantioselectivity and excellent functional group tolerance. Remarkably, the hydrogenation proceeds smoothly at the gram scale, and the products can be transformed into several chiral potential building blocks without loss of optical purity. This work provides a new strategy for asymmetric hydrogenation of esters under base-free conditions.

SUBMITTER: Wang H

PROVIDER: S-EPMC11253110 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature

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Palladium-catalyzed asymmetric hydrogenation of lactones under base-free conditions.

Wang Han H Xun Shan-Shan SS Yu Chang-Bin CB Zhou Yong-Gui YG

Chemical science 20240612 28

Asymmetric hydrogenation of esters through homogeneous catalysis is a significantly important transformation in organic synthesis. The systems developed so far mainly focused on chiral iridium and ruthenium catalysts, which required a base to facilitate the activity. Herein, we present a palladium-catalyzed asymmetric hydrogenation of lactones under base-free conditions through dynamic kinetic resolution and kinetic resolution. The reaction exhibits high enantioselectivity and excellent function ...[more]

PMID: 39027297

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