Literature DB >> 31647668

Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with pivZPhos as the Ligand.

Linglin Wu1, Olga Zatolochnaya1, Bo Qu1, Ling Wu1, Lucille A Wells2, Marisa C Kozlowski2, Chris H Senanayake1, Jinhua J Song1, Yongda Zhang1.   

Abstract

A Cu-catalyzed enantioselective aminoboration of E-vinylarenes with pivZPhos as a ligand is reported. Enantioenriched aminoborates are prepared with excellent regio- and enantioselectivities up to >99:1 er under the optimized conditions. The utility of the current method was further established by rapid conversion of an adduct to a chiral benzo[f][1,4]oxazepine. A model for the stereochemistry of the asymmetric aminoboration process, which agrees with the experimental outcomes, was generated by computational analysis of the systems.

Entities:  

Year:  2019        PMID: 31647668      PMCID: PMC6858512          DOI: 10.1021/acs.orglett.9b03328

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  18 in total

1.  Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes.

Authors:  Kodai Kato; Koji Hirano; Masahiro Miura
Journal:  Chemistry       Date:  2018-03-23       Impact factor: 5.236

2.  Copper-Catalyzed Regio- and Stereoselective Aminoboration of Alkenylboronates.

Authors:  Daiki Nishikawa; Koji Hirano; Masahiro Miura
Journal:  Org Lett       Date:  2016-09-20       Impact factor: 6.005

3.  Copper-Catalysed Aminoboration of Vinylarenes with Hydroxylamine Esters-A Computational Mechanistic Study.

Authors:  Sven Tobisch
Journal:  Chemistry       Date:  2017-11-20       Impact factor: 5.236

Review 4.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

5.  Enantioselective Nickel-Catalyzed Mizoroki-Heck Cyclizations To Generate Quaternary Stereocenters.

Authors:  Jean-Nicolas Desrosiers; Jialin Wen; Sergei Tcyrulnikov; Soumik Biswas; Bo Qu; Liana Hie; Dmitry Kurouski; Ling Wu; Nelu Grinberg; Nizar Haddad; Carl A Busacca; Nathan K Yee; Jinhua J Song; Neil K Garg; Xumu Zhang; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2017-06-12       Impact factor: 6.005

Review 6.  Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes.

Authors:  John R Coombs; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-13       Impact factor: 15.336

7.  A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination.

Authors:  Sheng Guo; Jeffrey C Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-11-08       Impact factor: 15.419

8.  Enantioselective Intramolecular Copper-Catalyzed Borylacylation.

Authors:  Andrew Whyte; Katherine I Burton; Jingli Zhang; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-21       Impact factor: 15.336

9.  Rhodium-catalysed syn-carboamination of alkenes via a transient directing group.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Nature       Date:  2015-10-21       Impact factor: 49.962

10.  Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution.

Authors:  Olga V Zatolochnaya; Sonia Rodríguez; Yongda Zhang; Kendricks S Lao; Sergei Tcyrulnikov; Guisheng Li; Xiao-Jun Wang; Bo Qu; Soumik Biswas; Hari P R Mangunuru; Daniel Rivalti; Joshua D Sieber; Jean-Nicolas Desrosiers; Joyce C Leung; Nelu Grinberg; Heewon Lee; Nizar Haddad; Nathan K Yee; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Chem Sci       Date:  2018-04-23       Impact factor: 9.825

View more
  1 in total

Review 1.  Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors:  Weichao Xue; Martin Oestreich
Journal:  ACS Cent Sci       Date:  2020-07-09       Impact factor: 14.553

  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.