Organocatalyst-Controlled Highly α′-Selective Deuteration and α,α′-Deuteration of Enones
Abstract
Herein, we report organocatalyst-controlled deuteration of enones at the α′-position or at both the α- and α′-positions under mild reaction conditions using D 2 O as the deuterium source. The key to the success of this protocol is the appropriate selection of the catalytic system. A quinine-derived primary amine-benzoic acid catalytic composite deuterated the α′-position of enones with high selectivity. On the other hand, the ( 1S, 2S )-1,2-diphenylethane-1,2-diamine-benzoic acid catalytic system promotes deuteration at both the α- and α′-positions of enones. In addition, this flexible protocol also features a broad substrate scope (>48 examples), including drug molecules and natural products, mild reaction conditions, and facile scalability. A working mechanistic pathway is also proposed.
Fields of Study & Subjects
Chemical Reactions and Isotopes
Asymmetric Hydrogenation and Catalysis
Fluorine in Organic Chemistry
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 22
- Pages
- 7454–7463
- Publication date
- 27 May 2026
- Language
- EN