Literature DB >> 24500845

Enantioselective palladium-catalyzed insertion of α-aryl-α-diazoacetates into the O-H bonds of phenols.

Xiu-Lan Xie1, Shou-Fei Zhu, Jun-Xia Guo, Yan Cai, Qi-Lin Zhou.   

Abstract

A palladium-catalyzed asymmetric O-H insertion reaction was developed. Palladium complexes with chiral spiro bisoxazoline ligands promoted the insertion of α-aryl-α-diazoacetates into the O-H bond of phenols with high yield and excellent enantioselectivity under mild reaction conditions. This palladium-catalyzed asymmetric O-H insertion reaction provided an efficient and highly enantioselective method for the preparation of synthetically useful optically active α-aryl-α-aryloxyacetates.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; bisoxazoline ligands; carbenes; palladium; α-aryl-α-aryloxyacetates

Year:  2014        PMID: 24500845     DOI: 10.1002/anie.201309820

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  9 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Overcoming O-H Insertion to Para-Selective C-H Functionalization of Free Phenols: Rh(II)/Xantphos Catalyzed Geminal Difunctionalization of Diazo Compounds.

Authors:  Yang Yang; Bin Lu; Guiqing Xu; Xiaoming Wang
Journal:  ACS Cent Sci       Date:  2022-04-20       Impact factor: 18.728

3.  Enantioselective synthesis of α-alkenyl α-amino acids via N-H insertion reactions.

Authors:  Jun-Xia Guo; Ting Zhou; Bin Xu; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2015-10-28       Impact factor: 9.825

4.  Asymmetric synthesis of isochromanone derivatives via trapping carboxylic oxonium ylides and aldol cascade.

Authors:  Jiawen Lang; Siyuan Wang; Changli He; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2021-12-27       Impact factor: 9.825

5.  Copper-catalyzed asymmetric cyclization of alkenyl diynes: method development and new mechanistic insights.

Authors:  Xin-Qi Zhu; Pan Hong; Yan-Xin Zheng; Ying-Ying Zhen; Feng-Lin Hong; Xin Lu; Long-Wu Ye
Journal:  Chem Sci       Date:  2021-06-11       Impact factor: 9.825

6.  Origins of unique gold-catalysed chemo- and site-selective C-H functionalization of phenols with diazo compounds.

Authors:  Yuan Liu; Zhunzhun Yu; John Zenghui Zhang; Lu Liu; Fei Xia; Junliang Zhang
Journal:  Chem Sci       Date:  2015-11-27       Impact factor: 9.825

7.  Photoinduced Proton-Transfer Reactions for Mild O-H Functionalization of Unreactive Alcohols.

Authors:  Sripati Jana; Zhen Yang; Fang Li; Claire Empel; Junming Ho; Rene M Koenigs
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-25       Impact factor: 15.336

Review 8.  Generation of Tosyl Azide in Continuous Flow Using an Azide Resin, and Telescoping with Diazo Transfer and Rhodium Acetate-Catalyzed O-H Insertion.

Authors:  Rosella M O'Mahony; Denis Lynch; Katie S O'Callaghan; Stuart G Collins; Anita R Maguire
Journal:  Org Process Res Dev       Date:  2021-11-30       Impact factor: 3.317

9.  Proton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols.

Authors:  Claire Empel; Chao Pei; Feifei He; Sripati Jana; Rene M Koenigs
Journal:  Chemistry       Date:  2022-02-17       Impact factor: 5.020

  9 in total

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