Literature DB >> 23503498

A novel catalytic asymmetric route towards skipped dienes with a methyl-substituted central stereogenic carbon.

Yange Huang1, Martín Fañanás-Mastral, Adriaan J Minnaard, Ben L Feringa.   

Abstract

A highly efficient method for the enantioselective synthesis of 1,4-dienes (skipped dienes) with a methyl-substituted central stereogenic carbon using copper-catalysed asymmetric allylic alkylation of diene bromides was developed. Excellent regio- and enantioselectivity (up to 97 : 3 SN2'/SN2 ratio and 99% ee) were achieved with broad substrate scope.

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Year:  2013        PMID： 23503498     DOI： 10.1039/c3cc41021h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  7 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  A New Paradigm in Enantioselective Cobalt Catalysis: Cationic Cobalt(I) Catalysts for Heterodimerization, Cycloaddition, and Hydrofunctionalization Reactions of Olefins.

Authors:  Souvagya Biswas; Mahesh M Parsutkar; Stanley M Jing; Vinayak V Pagar; James H Herbort; T V RajanBabu
Journal:  Acc Chem Res       Date:  2021-11-30       Impact factor: 22.384

3.  Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

Authors:  Michelle H Lacoske; Jing Xu; Noel Mansour; Chao Gao; Emmanuel A Theodorakis
Journal:  Org Chem Front       Date:  2015-04-01       Impact factor: 5.281

4.  Asymmetric Catalysis with Ethylene. Synthesis of Functionalized Chiral Enolates.

Authors:  Souvagya Biswas; Jordan P Page; Kendra R Dewese; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

5.  Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes.

Authors:  Ghina'a I Abu Deiab; Mohammed H Al-Huniti; I F Dempsey Hyatt; Emma E Nagy; Kristen E Gettys; Sommayah S Sayed; Christine M Joliat; Paige E Daniel; Rupa M Vummalaneni; Andrew T Morehead; Andrew L Sargent; Mitchell P Croatt
Journal:  Beilstein J Org Chem       Date:  2017-02-28       Impact factor: 2.883

6.  Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.

Authors:  Andrea Chaves-Pouso; Andrés M Álvarez-Constantino; Martín Fañanás-Mastral
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-21       Impact factor: 16.823

7.  1,2-Carboboration of Arylallenes by In Situ Generated Alkenylboranes for the Synthesis of 1,4-Dienes.

Authors:  Arthur Averdunk; Max Hasenbeck; Tizian Müller; Jonathan Becker; Urs Gellrich
Journal:  Chemistry       Date:  2022-04-21       Impact factor: 5.020
  7 in total

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