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

文献情報

出版日 2019-11-25

DOI 10.1039/C9QO01047E

インパクトファクター 5.281

著者

Zhichao Xiong, Jiangyan Tian, Peng Xue, Xumu Zhang

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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