American Chemical Society
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Asymmetric Synthesis of P‑Stereogenic Diarylphosphinites by Palladium-Catalyzed Enantioselective Addition of Diarylphosphines to Benzoquinones

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journal contribution
posted on 2014-04-02, 00:00 authored by Yinhua Huang, Yongxin Li, Pak-Hing Leung, Tamio Hayashi
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 °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.