Literature DB >> 27286229

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

Zhijian Huang1, Xuan Huang1, Baosheng Li1, Chengli Mou2, Song Yang2, Bao-An Song2, Yonggui Robin Chi2,1.   

Abstract

A carbene-catalyzed desymmetrization of prochiral bisphenol compounds bearing remote P-stereogenic 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.

Entities:  

Year:  2016        PMID： 27286229     DOI： 10.1021/jacs.6b04624

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


  7 in total

1.  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

2.  NHC-catalyzed atropoenantioselective synthesis of axially chiral biaryl amino alcohols via a cooperative strategy.

Authors:  Gongming Yang; Donghui Guo; Di Meng; Jian Wang
Journal:  Nat Commun       Date:  2019-07-11       Impact factor: 14.919

3.  Synthesis of N-Heteroarenemethyl Esters via C-C Bond Cleavage of Acyl Cyanides Under Transition Metal-Free Conditions.

Authors:  Miao Lai; Fangyao Su; Jingyi Hu; Mengzhuo Wang; Mingqin Zhao; Ganlin Zhang
Journal:  Front Chem       Date:  2022-01-27       Impact factor: 5.221

4.  Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis.

Authors:  Zhouli Hu; Chenlong Wei; Qianqian Shi; Xianfang Hong; Jinhua Liu; Xiangui Zhou; Jinna Han; Wei Cao; Ashis Kumar Gupta; Xiaoxiang Zhang; Donghui Wei; Zhenqian Fu; Wei Huang
Journal:  Nat Commun       Date:  2022-07-13       Impact factor: 17.694

5.  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

6.  Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines.

Authors:  Rodolphe Beaud; Robert J Phipps; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2016-09-30       Impact factor: 15.419

7.  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
  7 in total

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