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Synfacts 2025; 21(01): 72
DOI: 10.1055/a-2467-4591
Organo- and Biocatalysis

Enantioselective Hydrogen Atom Abstraction Catalysis

Contributor(s):
Benjamin List 
,
Nils Frank 
Lahdenperä ASK, Dhankhar J, Davies DJ, Lam NYS, Bacoş PD, de la Vega-Hernandez K, Phipps RJ *. University of Cambridge, UK
A Chiral Hydrogen Atom Abstraction Catalyst for the Enantioselective Epimerization of meso-Diols.

Science 2024;
386: 42-49
DOI: 10.1126/science.adq8029
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Keywords

hydrogen atom abstraction - chinchona - quinuclidines - desymmetrization

Significance

Lahdenperä et al. present the chiral quinuclidine hydrogen atom abstraction catalyst 1, engineered from the cinchona alkaloid natural chiral pool. This work desymmetrizes cyclic and acylic meso-1,2- and 1,3-diols towards trans-diols and Giese acceptor-intercepted products in 31–98 % yield and excellent enantioselectivities.


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Comment

While enantioselective hydrogen atom donations are well established, this report capitalizes on enantioselective hydrogen atom abstraction. The subsequent thiol-mediated hydrogen atom donation delivers the enantioenriched trans-diol and regained meso-starting material.


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Publication History

Article published online:
20 December 2024

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