Literature DB >> 19334029

Enantioselective Friedel-Crafts reactions in water using a DNA-based catalyst.

Arnold J Boersma1, Ben L Feringa, Gerard Roelfes.   

Abstract

Taking the plunge: The first example of a Lewis acid catalyzed asymmetric Friedel-Crafts alkylation with olefins in water is described. By using loadings of a DNA-based copper catalyst as low as 0.15 mol %, good yields and excellent enantioselectivities were obtained in the reaction of alpha,beta-unsaturated 2-acyl imidazoles with heteroaromatic pi nucleophiles. dmbpy = 4,4'-dimethyl-2,2'-bipyridine.

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Year:  2009        PMID： 19334029     DOI： 10.1002/anie.200900371

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


  21 in total

1.  Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

Authors:  Madeleine E Kieffer; Lindsay M Repka; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2012-03-05       Impact factor: 15.419

2.  Microwave-induced inactivation of DNA-based hybrid catalyst in asymmetric catalysis.

Authors:  Hua Zhao; Kai Shen
Journal:  Int J Biol Macromol       Date:  2015-12-19       Impact factor: 6.953

3.  DNA-Based Asymmetric Catalysis: Role of Ionic Solvents and Glymes.

Authors:  Hua Zhao; Kai Shen
Journal:  RSC Adv       Date:  2014-01-01       Impact factor: 3.361

Review 4.  DNA as a versatile chemical component for catalysis, encoding, and stereocontrol.

Authors:  Scott K Silverman
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

5.  G-quadruplex DNA-based asymmetric catalysis of michael addition: Effects of sonication, ligands, and co-solvents.

Authors:  Hua Zhao; Kai Shen
Journal:  Biotechnol Prog       Date:  2016-05-04

6.  Rh(I)-bisphosphine-catalyzed asymmetric, intermolecular hydroheteroarylation of α-substituted acrylate derivatives.

Authors:  Claire M Filloux; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-12-29       Impact factor: 15.419

7.  DNA-Accelerated Catalysis of Carbene-Transfer Reactions by a DNA/Cationic Iron Porphyrin Hybrid.

Authors:  Ana Rioz-Martínez; Jens Oelerich; Nathalie Ségaud; Gerard Roelfes
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-12       Impact factor: 15.336

8.  Novel artificial metalloenzymes by in vivo incorporation of metal-binding unnatural amino acids.

Authors:  Ivana Drienovská; Ana Rioz-Martínez; Apparao Draksharapu; Gerard Roelfes
Journal:  Chem Sci       Date:  2014-10-09       Impact factor: 9.825

9.  Chiral cis-iron(ii) complexes with metal- and ligand-centered chirality for highly regio- and enantioselective alkylation of N-heteroaromatics.

Authors:  Jinhu Wei; Bei Cao; Chun-Wai Tse; Xiao-Yong Chang; Cong-Ying Zhou; Chi-Ming Che
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

10.  Modular assembly of a Pd catalyst within a DNA scaffold for the amplified colorimetric and fluorimetric detection of nucleic acids.

Authors:  Deepak K Prusty; Minseok Kwak; Jur Wildeman; Andreas Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-17       Impact factor: 15.336
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