Literature DB >> 25145856

Kinetic resolution of 1,1'-biaryl-2,2'-diols and amino alcohols through NHC-catalyzed atroposelective acylation.

Shenci Lu1, Si Bei Poh, Yu Zhao.   

Abstract

We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1'-biaryl-2,2'-diols and amino alcohols to provide them in uniformly ≥99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-heterocyclic carbene; acylation; axial chirality; enantioselectivity; kinetic resolution

Mesh：

Substances：

Year:  2014        PMID： 25145856     DOI： 10.1002/anie.201406192

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


  14 in total

1.  Catalytic enantioselective synthesis of atropisomeric biaryls by a cation-directed O-alkylation.

Authors:  John D Jolliffe; Roly J Armstrong; Martin D Smith
Journal:  Nat Chem       Date:  2017-01-23       Impact factor: 24.427

2.  Discovery and enantiocontrol of axially chiral urazoles via organocatalytic tyrosine click reaction.

Authors:  Ji-Wei Zhang; Jin-Hui Xu; Dao-Juan Cheng; Chuan Shi; Xin-Yuan Liu; Bin Tan
Journal:  Nat Commun       Date:  2016-02-11       Impact factor: 14.919

3.  Bifunctional organocatalysts for the asymmetric synthesis of axially chiral benzamides.

Authors:  Ryota Miyaji; Yuuki Wada; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  Beilstein J Org Chem       Date:  2017-08-02       Impact factor: 2.883

4.  Organocatalytic atroposelective synthesis of axially chiral styrenes.

Authors:  Sheng-Cai Zheng; San Wu; Qinghai Zhou; Lung Wa Chung; Liu Ye; Bin Tan
Journal:  Nat Commun       Date:  2017-05-03       Impact factor: 14.919

Review 5.  N-Heterocyclic-Carbene-Catalyzed Domino Reactions via Two or More Activation Modes.

Authors:  Xiang-Yu Chen; Sun Li; Fabrizio Vetica; Mukesh Kumar; Dieter Enders
Journal:  iScience       Date:  2018-04-05

6.  Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion.

Authors:  Benjamin A Jones; Tudor Balan; John D Jolliffe; Craig D Campbell; Martin D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-05       Impact factor: 15.336

7.  Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles.

Authors:  Lei Zhang; Shao-Hua Xiang; Jun Joelle Wang; Jian Xiao; Jun-Qi Wang; Bin Tan
Journal:  Nat Commun       Date:  2019-02-04       Impact factor: 14.919

8.  Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.

Authors:  Yu-Long Hu; Zhe Wang; Hui Yang; Jie Chen; Zi-Bo Wu; Yibo Lei; Ling Zhou
Journal:  Chem Sci       Date:  2019-05-20       Impact factor: 9.825

9.  Practical access to axially chiral sulfonamides and biaryl amino phenols via organocatalytic atroposelective N-alkylation.

Authors:  Shenci Lu; Shawn Voon Hwee Ng; Kaitlyn Lovato; Jun-Yang Ong; Si Bei Poh; Xiao Qian Ng; László Kürti; Yu Zhao
Journal:  Nat Commun       Date:  2019-07-11       Impact factor: 14.919

10.  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
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