Literature DB >> 24771670

The use of silyl ketene acetals and enol ethers in the catalytic enantioselective alkylative ring opening of oxa/aza bicyclic alkenes.

Lei Zhang1, Christine M Le, Mark Lautens.   

Abstract

Silyl ketene acetals and enol ethers are employed as reactive and functional group tolerant nucleophiles in the enantioselective rhodium-catalyzed alkylative ring opening of a diverse class of oxa/azabicyclic alkenes. This method provides access to enantioenriched dihydronaphthalene and cyclohexene scaffolds, which have the potential to be derivatized toward core motifs of naphthoquinone and sesquiterpene natural products.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; rhodium; silyl ketene acetals; strained molecules

Mesh:

Substances:

Year:  2014        PMID: 24771670     DOI: 10.1002/anie.201400218

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


  5 in total

1.  Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis.

Authors:  Youran Luo; Álvaro Gutiérrez-Bonet; Jennifer K Matsui; Madeline E Rotella; Ryan Dykstra; Osvaldo Gutierrez; Gary A Molander
Journal:  ACS Catal       Date:  2019-08-28       Impact factor: 13.084

2.  Iridium-Catalyzed Enantioselective Allylic Substitution of Aliphatic Esters with Silyl Ketene Acetals as the Ester Enolates.

Authors:  Xingyu Jiang; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-27       Impact factor: 15.336

3.  Nickel-Catalyzed Dearomative trans-1,2-Carboamination.

Authors:  Lucas W Hernandez; Ulrich Klöckner; Jola Pospech; Lilian Hauss; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-03-23       Impact factor: 15.419

4.  Three-Component 1,2-Carboamidation of Bridged Bicyclic Alkenes via RhIII-Catalyzed Addition of C-H Bonds and Amidating Reagents.

Authors:  Daniel S Brandes; Ana Sirvent; Brandon Q Mercado; Jonathan A Ellman
Journal:  Org Lett       Date:  2021-03-19       Impact factor: 6.005

5.  Mechanism, reactivity, and regioselectivity in rhodium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes: a DFT Investigation.

Authors:  Zheng-Hang Qi; Yi Zhang; Yun Gao; Ye Zhang; Xing-Wang Wang; Yong Wang
Journal:  Sci Rep       Date:  2017-01-11       Impact factor: 4.379

  5 in total

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