Enantioselective Imine Reduction Catalyzed by Phosphenium Ions
Journal of the American Chemical Society2019Vol. 141(36), pp. 14083–14088
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Travis Lundrigan, Erin N. Welsh, Toren Hynes, Chieh‐Hung Tien, Matt R. Adams, Kayelani R. Roy, Katherine N. Robertson, Alexander W. H. Speed
Abstract
The first use of phosphenium cations in asymmetric catalysis is reported. A diazaphosphenium triflate, prepared in two or three steps on a multigram scale from commercially available materials, catalyzes the hydroboration or hydrosilylation of cyclic imines with enantiomeric ratios of up to 97:3. Catalyst loadings are as low as 0.2 mol %. Twenty-two aryl/heteroaryl pyrrolidines and piperidines were prepared using this method. Imines containing functional groups such as thiophenes or pyridyl rings that can challenge transition-metal catalysts were reduced employing these systems.
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