4.8 Article

Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 8, Pages 3065-3071

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b12254

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Funding

  1. Natural Sciences and Engineering Research Council of Canada (NSERC)
  2. GreenCentre Canada
  3. University of Alberta

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High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized alpha-phenoxy and related amides at room temperature under 4 atm H-2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

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