Diastereo- and Enantioselective Nickel-Catalyzed Intramolecular Reductive Cyclization of Unactivated Alkenes and Aldehydes
Abstract
Catalytic reductive coupling of unsaturated hydrocarbons with carbonyl compounds provides a streamlined alternative to stoichiometric organometallic additions, yet asymmetric variants that directly engage unactivated alkenes remain limited. Here we report a diastereo- and enantioselective nickel-catalyzed intramolecular reductive cyclization of unactivated alkenes and aldehydes. Using a chiral monodentate phosphoramidite ligand and triethylborane as the terminal reductant, the method delivers substituted cyclic alcohols as single diastereomers in up to 98% yield and up to 99% ee, with broad functional-group tolerance including halides, free alcohols, esters, and boronic esters. Applications to bioactive-molecule synthesis are demonstrated, and DFT studies support an enantiodetermining oxidative cyclization pathway.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Organoboron and organosilicon chemistry
Asymmetric Hydrogenation and Catalysis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 7
- Pages
- 2512–2517
- Publication date
- 5 February 2026
- Language
- EN