4.8 Article

Enantioselective and Diastereoselective Ir-Catalyzed Hydrogenation of alpha-Substituted beta-Ketoesters via Dynamic Kinetic Resolution

Journal

ORGANIC LETTERS
Volume 20, Issue 7, Pages 1888-1892

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b00433

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Funding

  1. Shenzhen Tech-Innovation Program from the Shenzhen Science, Technology and Innovation Commission
  2. Shenzhen Free Exploration Fund
  3. Shenzhen Research Grants [JSGG20160608140847864]

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An iridium/f-amphol catalytic system for the enantioselective hydrogenation of alpha-substituted beta-ketoesters via dynamic kinetic resolution is reported. The desired anti products were obtained in high yields (up to 98%) with good diastereoselectivity (up to 96:4 diastereometic ratio (dr)) and excellent enantioselectivity (up to >99% enantiomeric excess (ee)). A catalytic model is proposed to explain the stereoselectivity.

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