Literature DB >> 19623343

Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reactions.

Shu-Li You1, Quan Cai, Mi Zeng.   

Abstract

The asymmetric Friedel-Crafts reaction is one of the most powerful methods to synthesize optically active aromatic compounds. Particularly, the Friedel-Crafts alkylation of arenes with unsaturated compounds activated by chiral Brønsted acids provides direct access to enantiopure aromatic derivatives with perfect atom economy. In this tutorial review, recent progress in the development of chiral Brønsted acid-catalyzed asymmetric Friedel-Crafts reactions is presented.

Entities:  

Year:  2009        PMID： 19623343     DOI： 10.1039/b817310a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN： 0306-0012            Impact factor:   54.564


  34 in total

1.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

2.  Bifunctional cinchona alkaloid-squaramide-catalyzed highly enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones.

Authors:  Arun K Ghosh; Bing Zhou
Journal:  Tetrahedron Lett       Date:  2013-07-03       Impact factor: 2.415

3.  Chemoenzymatic synthesis of each enantiomer of orthogonally protected 4,4-difluoroglutamic acid: a candidate monomer for chiral Brønsted acid peptide-based catalysts.

Authors:  Yang Li; Scott J Miller
Journal:  J Org Chem       Date:  2011-11-09       Impact factor: 4.354

4.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

5.  N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.

Authors:  Xiaodan Zhao; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

6.  Concise Total Synthesis of (+)-Gliocladins B and C.

Authors:  Nicolas Boyer; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2012-03-30       Impact factor: 9.825

7.  Iridium-catalyzed regio- and enantioselective N-allylation of indoles.

Authors:  Levi M Stanley; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Asymmetric one-pot sequential Friedel-Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme.

Authors:  Kengo Akagawa; Ryota Umezawa; Kazuaki Kudo
Journal:  Beilstein J Org Chem       Date:  2012-08-17       Impact factor: 2.883

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.  Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans.

Authors:  Jiahuan Peng; Da-Ming Du
Journal:  Beilstein J Org Chem       Date:  2013-06-24       Impact factor: 2.883
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