RuPHOX-Ru-Catalyzed Asymmetric Chemoselective Hydrogenation of α-Methylene-γ/δ-carbonyl Carboxylic Acids
Abstract
A highly efficient RuPHOX-Ru-catalyzed asymmetric chemoselective hydrogenation of the C═C bond in α-methylene-γ/δ-carbonyl carboxylic acids has been developed (46 examples), providing the desired chiral α-methyl-γ/δ-carbonyl carboxylic acids in high yields (up to 99%) with excellent enantioselectivities (almost ≥99% ee). The protocol can be performed on a gram scale with a low catalyst loading (up to 11 000 S/C) and demonstrates significant synthetic utility in the preparation of bioactive molecules, including the synthesis of anti-inflammatory and analgesic drug ( S )-flobufen. Mechanistic studies revealed that H 2 is the sole hydrogen source for the hydrogenation and the use of PPh 3 as an additive is beneficial for the excellent enantioselectivity.
Fields of Study & Subjects
Asymmetric Hydrogenation and Catalysis
Surface Chemistry and Catalysis
Catalysis for Biomass Conversion
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 4
- Pages
- 1317–1323
- Publication date
- 16 January 2026
- Language
- EN