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

Author:
Holmes, Michael, Nguyen, Khoa D., Schwartz, Leyah A., Luong, Tom, Krische, Michael J.
Source:
Journal of the American Chemical Society 2017 v.139 no.24 pp. 8114-8117
ISSN:
1520-5126
Subject:
allene, byproducts, carbon-hydrogen bond activation, catalysts, enantioselectivity, hydrogen, iridium, methanol, positional isomers
Abstract:
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.
Agid:
6031072