4.8 Article

Access to P-Stereogenic Phosphinates via N-Heterocyclic Carbene-Catalyzed Desymmetrization of Bisphenols

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 24, Pages 7524-7527

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b04624

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Funding

  1. Singapore National Research Foundation
  2. GlaxoSmithKline
  3. Ministry of Education of Singapore
  4. Nanyang Technological University
  5. China's Ministry of Education
  6. National Key Program for Basic Research [2010CB 126105]
  7. Thousand Talent Plan
  8. National Natural Science Foundation of China [21132003, 21472028]
  9. Guizhou Province Returned Oversea Student Science and Technology Activity Program
  10. Science and Technology Department of Guizhou Province
  11. Guizhou University

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A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereo genic centers is disclosed. The catalytic reactions can be performed on gram scales with 1 mol % N-heterocyclic carbene (NHC) catalyst, providing efficient access to enantiomerically enriched P-stereogenic phosphinates. The chiral phosphinates prepared with our method can find widespread applications as asymmetric organic catalysts and ligands.

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