Literature DB >> 24635477

Asymmetric synthesis of P-stereogenic diarylphosphinites by palladium-catalyzed enantioselective addition of diarylphosphines to benzoquinones.

Yinhua Huang1, Yongxin Li, Pak-Hing Leung, Tamio Hayashi.   

Abstract

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.

Entities:  

Year:  2014        PMID: 24635477     DOI: 10.1021/ja501007t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  Brønsted acid catalyzed phosphoramidic acid additions to alkenes: diastereo- and enantioselective halogenative cyclizations for the synthesis of C- and P-chiral phosphoramidates.

Authors:  Yasunori Toda; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2014-10-14       Impact factor: 15.419

2.  Tailored trisubstituted chiral Cp x RhIII catalysts for kinetic resolutions of phosphinic amides.

Authors:  Y Sun; N Cramer
Journal:  Chem Sci       Date:  2018-02-05       Impact factor: 9.825

3.  Electrochemical oxidative N-H/P-H cross-coupling with H2 evolution towards the synthesis of tertiary phosphines.

Authors:  Yong Yuan; Xue Liu; Jingcheng Hu; Pengjie Wang; Shengchun Wang; Hesham Alhumade; Aiwen Lei
Journal:  Chem Sci       Date:  2022-02-14       Impact factor: 9.825

4.  Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution.

Authors:  Haile Qiu; Qiang Dai; Jiafeng He; Wenbo Li; Junliang Zhang
Journal:  Chem Sci       Date:  2020-09-02       Impact factor: 9.825

5.  Enantioselective synthesis of P-chiral tertiary phosphine oxides with an ethynyl group via Cu(i)-catalyzed azide-alkyne cycloaddition.

Authors:  Ren-Yi Zhu; Long Chen; Xiao-Si Hu; Feng Zhou; Jian Zhou
Journal:  Chem Sci       Date:  2019-11-06       Impact factor: 9.825

  5 in total

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