Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C–H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation

Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C–H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation
Khoa D. Nguyen, Michael Holmes, Michael J. Krische, Leyah A. Schwartz, Tom Luong
Using an iridium catalyst modified by PhanePhos, CF3-allenes react with methanol to form branched products of hydrohydroxymethylation as single regioisomers with excellent levels of enantiomeric enrichment. This hydrogen autotransfer process enables catalytic enantioselective formation of acyclic CF3-bearing all-carbon quaternary stereocenters in the absence of stoichiometric metals or byproducts.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b04374

DOI: 10.1021/jacs.7b04374

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