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Issue 1, 2020
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Enantioselective synthesis of chiral multicyclic γ-lactones via dynamic kinetic resolution of racemic γ-keto carboxylic acids

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Abstract

Ru-Catalyzed asymmetric transfer hydrogenation of γ-keto carboxylic acids has been achieved by using the formic acid–triethylamine azeotrope as the hydrogen source, affording chiral multicyclic γ-lactones in high yields with excellent diastereo- and enantioselectivities (up to 92% yield, >20 : 1 dr and 99% ee). This method provides a highly efficient approach to obtain valuable multicyclic γ-lactones through a reduction/lactonization sequence. Moreover, a concise synthetic route to obtain bioactive molecules (+)-GR24 and (+)-epi-GR24 has also been developed by using this methodology as a key step.

Graphical abstract: Enantioselective synthesis of chiral multicyclic γ-lactones via dynamic kinetic resolution of racemic γ-keto carboxylic acids

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Article information


Submitted
24 Aug 2019
Accepted
12 Nov 2019
First published
25 Nov 2019

Org. Chem. Front., 2020,7, 104-108
Article type
Research Article

Enantioselective synthesis of chiral multicyclic γ-lactones via dynamic kinetic resolution of racemic γ-keto carboxylic acids

Z. Xiong, J. Tian, P. Xue, X. Zhang and H. Lv, Org. Chem. Front., 2020, 7, 104
DOI: 10.1039/C9QO01047E

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