Diastereo-divergent synthesis of chiral hindered ethers via a synergistic calcium(II)/gold(I) catalyzed cascade hydration/1,4-addition reaction

Xiangfeng Lin, Xia Mu, Hongqiang Cui, Qian Li, Zhaochi Feng, Yan Liu (), Guohui Li () and Can Li ()
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Xiangfeng Lin: Chinese Academy of Sciences
Xia Mu: Chinese Academy of Science
Hongqiang Cui: Chinese Academy of Science
Qian Li: Chinese Academy of Sciences
Zhaochi Feng: Chinese Academy of Sciences
Yan Liu: Chinese Academy of Sciences
Guohui Li: University of Chinese Academy of Sciences
Can Li: Chinese Academy of Sciences

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract Hindered ethers are ubiquitous in natural products and bioactive molecules. However, developing an efficient method for the stereocontrolled synthesis of all stereoisomers of chiral hindered ethers is highly desirable but challenging. Here we show a strategy that utilizes in situ-generated water as a nucleophile in an asymmetric cascade reaction involving two highly reactive intermediates, 3-furyl methyl cations and ortho-quinone methides (o-QMs), to synthesize chiral hindered ethers. The Ca(II)/Au(I) synergistic catalytic system enables the control of diastereoselectivity and enantioselectivity by selecting suitable chiral phosphine ligands in this cascade hydration/1,4-addition reaction, affording all four stereoisomers of a diverse range of chiral tetra-aryl substituted ethers with high diastereoselectivities (up to >20/1) and enantioselectivities (up to 95% ee). This work provides an example of chiral Ca(II)/Au(I) bimetallic catalytic system controlling two stereogenic centers via a cascade reaction in a single operation.

Date: 2024
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DOI: 10.1038/s41467-024-47951-9

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