4.8 Article

Asymmetric Synthesis of P-Stereogenic Diarylphosphinites by Palladium-Catalyzed Enantioselective Addition of Diarylphosphines to Benzoquinones

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 13, Pages 4865-4868

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja501007t

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Funding

  1. Nanyang Technological University
  2. National University of Singapore

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The reaction of phenyl(2,4,6-trimethylphenyl)phosphine with a substituted benzoquinone in the presence of a chiral phosphapalladacycle complex as a catalyst and triethylamine in chloroform at -45 degrees C proceeded in a new type of addition manner to give a high yield of a 4-hydroxyphenyl phenyl(2,4,6-trimethylphenyl)phosphinite with 98% enantioselectivity, which is a versatile intermediate readily convertible into various phosphines and their derivatives with high enantiomeric purity.

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