Literature DB >> 30191642

Enantioselective Functionalization of Enamides at the β-Carbon Center with Indoles.

Mirza A Saputra1, Binod Nepal1, Nitin S Dange1, Pu Du1, Frank R Fronczek1, Revati Kumar1, Rendy Kartika1.   

Abstract

We report an enantioconvergent approach for the functionalization of enamides at the β-carbon atom, which involves a chiral Brønsted acid induced tautomerization of 2-amidoallyl into 1-amidoallyl cations. These putative reactive intermediates were produced by ionization of racemic α-hydroxy enamides with a chiral Brønsted acid and captured with substituted indoles in a highly regio- and enantioselective manner.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  2-amidoallyl cations; Brønsted acids; asymmetric catalysis; indoles; tautomerization

Mesh：

Substances：

Year:  2018        PMID： 30191642      PMCID： PMC6407611          DOI： 10.1002/anie.201808764

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


  30 in total

1.  Chiral phosphoric acid catalyzed enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes: cooperative effect of 3 A molecular sieves.

Authors:  Junji Itoh; Kohei Fuchibe; Takahiko Akiyama
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Metal-free enantioselective electrophilic activation of allenamides: stereoselective dearomatization of indoles.

Authors:  Ciro Romano; Minqiang Jia; Magda Monari; Elisabetta Manoni; Marco Bandini
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-24       Impact factor: 15.336

3.  Copper-catalyzed enantioselective conjugate addition of dialkylzinc reagents to (2-pyridyl)sulfonyl imines of chalcones.

Authors:  Jorge Esquivias; Ramon Gómez Arrayás; Juan C Carretero
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

4.  Copper-catalyzed asymmetric conjugate addition of diethylzinc to alpha,beta-unsaturated imines derived from alpha-aminoacids. Enantioselective synthesis of gamma-substituted alpha-dehydroaminoesters.

Authors:  Francisco Palacios; Javier Vicario
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

5.  Rhodium catalyzed allene amination: diastereoselective synthesis of aminocyclopropanes via a 2-amidoallylcation intermediate.

Authors:  Armin H Stoll; Simon B Blakey
Journal:  J Am Chem Soc       Date:  2010-02-24       Impact factor: 15.419

6.  Cu(II)-catalyzed asymmetric boron conjugate addition to α,β-unsaturated imines in water.

Authors:  Taku Kitanosono; Pengyu Xu; Satoshi Isshiki; Lei Zhu; Shū Kobayashi
Journal:  Chem Commun (Camb)       Date:  2014-08-25       Impact factor: 6.222

7.  Chiral Brønsted acid catalyzed enantioselective Friedel-Crafts reaction of indoles and alpha-aryl enamides: construction of quaternary carbon atoms.

Authors:  Yi-Xia Jia; Jun Zhong; Shou-Fei Zhu; Can-Ming Zhang; Qi-Lin Zhou
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 8.  Asymmetric ion-pairing catalysis.

Authors:  Katrien Brak; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

9.  Enamine-iminium ion Nazarov cyclization of alpha-ketoenones.

Authors:  William F Bow; Ashok K Basak; Anais Jolit; David A Vicic; Marcus A Tius
Journal:  Org Lett       Date:  2010-02-05       Impact factor: 6.005

Review 10.  Enantioconvergent catalysis.

Authors:  Justin T Mohr; Jared T Moore; Brian M Stoltz
Journal:  Beilstein J Org Chem       Date:  2016-09-16       Impact factor: 2.883
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