Literature DB >> 27600090

General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening.

Nico Funken1, Felix Mühlhaus1, Andreas Gansäuer2.   

Abstract

We describe a regiodivergent epoxide opening (REO) featuring a catalyst-controlled synthesis of enantiomerically and diastereomerically highly enriched or pure syn- and anti- 1,3- and 1,4-difunctionalized building blocks from a common epoxide precursor. The REO is attractive for natural product synthesis and as a branching reaction for diversity-oriented synthesis with epoxides.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  electron transfer; epoxides; polyols; radicals; titanium

Year:  2016        PMID： 27600090     DOI： 10.1002/anie.201606064

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


  14 in total

1.  Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

Authors:  Kai Lang; Sebastian Torker; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2019-07-29       Impact factor: 15.419

2.  Asymmetric Radical Cyclopropanation of Dehydroaminocarboxylates: Stereoselective Synthesis of Cyclopropyl α-Amino Acids.

Authors:  Wan-Chen Cindy Lee; Duo-Sheng Wang; Congzhe Zhang; Jingjing Xie; Bo Li; X Peter Zhang
Journal:  Chem       Date:  2021-03-29       Impact factor: 25.832

3.  Radical differentiation of two ester groups in unsymmetrical diazomalonates for highly asymmetric olefin cyclopropanation.

Authors:  Jingyi Wang; Jingjing Xie; Wan-Chen Cindy Lee; Duo-Sheng Wang; X Peter Zhang
Journal:  Chem Catal       Date:  2021-12-29

4.  Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes.

Authors:  Xue Xu; Yong Wang; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Chem Sci       Date:  2017-03-31       Impact factor: 9.825

5.  Catalytic Radical Process for Enantioselective Amination of C(sp3 )-H Bonds.

Authors:  Chaoqun Li; Kai Lang; Hongjian Lu; Yang Hu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-16       Impact factor: 15.336

6.  Enantioconvergent Amination of Racemic Tertiary C-H Bonds.

Authors:  Kai Lang; Chaoqun Li; Isaac Kim; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2020-11-29       Impact factor: 15.419

7.  Enantioselective Radical Construction of 5-Membered Cyclic Sulfonamides by Metalloradical C-H Amination.

Authors:  Yang Hu; Kai Lang; Chaoqun Li; Joseph B Gill; Isaac Kim; Hongjian Lu; Kimberly B Fields; McKenzie Marshall; Qigan Cheng; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2019-11-01       Impact factor: 15.419

8.  A green strategy for the synthesis of sulfone derivatives of p-methylaminophenol: Kinetic evaluation and antibacterial susceptibility.

Authors:  Davood Nematollahi; Sadegh Khazalpour; Mina Ranjbar; Shima Momeni
Journal:  Sci Rep       Date:  2017-06-30       Impact factor: 4.379

9.  Asymmetric Radical Process for General Synthesis of Chiral Heteroaryl Cyclopropanes.

Authors:  Xiaoxu Wang; Jing Ke; Yiling Zhu; Arghya Deb; Yijie Xu; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-20       Impact factor: 16.383

10.  Controlling Enantioselectivity and Diastereoselectivity in Radical Cascade Cyclization for Construction of Bicyclic Structures.

Authors:  Congzhe Zhang; Duo-Sheng Wang; Wan-Chen Cindy Lee; Alexander M McKillop; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2021-07-14       Impact factor: 16.383
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