4.7 Article

Stereoselective Synthesis of 4-Substituted Cyclic Sulfamidate-5-Phosphonates by Using Rh-Catalyzed, Asymmetric Transfer Hydrogenation with Accompanying Dynamic Kinetic Resolution

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 17, Pages 8887-8902

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01434

Keywords

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Funding

  1. Ministry of Science, ICT & Future Planning of Korea through the National Research Foundation of Korea [NRF-2008-2004732]
  2. Korea Research Institute of Chemical Technology

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Dynamic kinetic resolution driven, asymmetric transfer hydrogenation of 4-substituted cyclic sulfamidate imine-5-phosphonates produces the corresponding cyclic sulfamidate-5-phosphonates. The process employs a HCO2H/Et3N mixture as the hydrogen source and the chiral Rh catalysts, (R,R)- or (S,S)-Cp*RhCl(TsDPEN), and it takes place at room temperature within 1 h with high yields and high levels of stereoselectivity.

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