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

Rasu, Loorthuraja; John, Jeremy M.; Stephenson, Elanna; Endean, Riley; Kalapugama, Suneth; Clément, Roxanne; Bergens, Steven H.

doi:10.1021/jacs.6b12254.s001

ja6b12254_si_001.pdf (13.12 MB)

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

journal contribution

posted on 2017-01-30, 00:00 authored by Loorthuraja Rasu, Jeremy M. John, Elanna Stephenson, Riley Endean, Suneth Kalapugama, Roxanne Clément, Steven H. Bergens

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 α-phenoxy and related amides at room temperature under 4 atm H₂ pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

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

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