4.8 Article

Rhodium-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated Carbonyl Compounds via Thiourea Hydrogen Bonding

Journal

ORGANIC LETTERS
Volume 18, Issue 18, Pages 4451-4453

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01812

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Funding

  1. China Scholarship Council
  2. National Natural Science Foundation of China [201506270049]

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The strategy of secondary interaction enables enantioselectivity for homogeneous hydrogenation. By in, troducing hydrogen bonding of substrates with thiourea from the ligand, alpha,beta-unsaturated carbonyl, compounds, such as amides and esters, are hydrogenated with high enantiomeric excess. The substrate scope for this chemical transformation is broad with various substituents at the beta-position. Control experiments revealed that each unit of the ligand ZhaoPhos is irreplaceable. No nonlinear effect was observed for this Rh/ZhaoPhos-catalyzed asymmetric hydrogenation.

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