Jump to main content
Jump to site search


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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Aug 2019, accepted on 12 Nov 2019 and first published on 25 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01047E
Org. Chem. Front., 2020, Advance Article

  •   Request permissions

    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, Advance Article , DOI: 10.1039/C9QO01047E

Search articles by author

Spotlight

Advertisements