Ruthenium-Catalyzed Formal Asymmetric Reductive Isomerization of α-Hydroxyenones

作者：Wennan Dong, Caiyi Ren, Lixuan Zhu, Peng Luo, Zhifei Zhao, Shouang Lan, Jinggong Liu, Shuang Yang, Qi Zhang, Xinqiang Fang · 发表于：ACS Catalysis · 年份：2024 · DOI：10.1021/acscatal.4c05378 · 被引用次数：7 · 研究领域：Asymmetric Hydrogenation and Catalysis、Catalysis for Biomass Conversion、Chemical Synthesis and Analysis

The isomerization of α-hydroxyketones (acyloins) is a fundamental transformation in carbohydrate chemistry. It has been found to play important roles in the metabolic processes of living organisms and organic synthesis. However, catalytic asymmetric acyloin isomerization remains a formidable challenge and has not been addressed. In this work, we report the unprecedented ruthenium-catalyzed formal asymmetric reductive isomerization of α-hydroxyenones. The protocol affords a variety of enantioenriched acyloins with a high level of enantioselectivities, and systematic mechanistic studies demonstrate a transformation involving the isomerization of α-hydroxyenones and ruthenium-catalyzed asymmetric transfer hydrogenation. The work provides an alternative approach to realizing the challenging catalytic asymmetric acyloin isomerization.