Literature DB >> 14743405

New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction.

Marco Bandini1, Alfonso Melloni, Achille Umani-Ronchi.   

Abstract

After more than 125 years, the Friedel-Crafts alkylation is still one of the most studied and most utilized reactions in organic synthesis. What is the secret of this astonishing success? Perhaps the great versatility in scope and applicability continues to justify its crucial role in the synthesis of more and more complex molecules. However, it has taken more than a century for asymmetric catalytic versions of this reaction to be developed and subsequently extended to a range of aromatic compounds and alkylating agents. Herein we review recent developments in the design and use of catalytic and stereoselective strategies for the alkylation of aromatic systems and synthesis of a wide range of polyfunctionalized enantiomerically enriched compounds.

Year:  2004        PMID: 14743405     DOI: 10.1002/anie.200301679

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


  22 in total

1.  Cu-catalyzed cross-dehydrogenative coupling: a versatile strategy for C-C bond formations via the oxidative activation of sp(3) C-H bonds.

Authors:  Zhiping Li; D Scott Bohle; Chao-Jun Li
Journal:  Proc Natl Acad Sci U S A       Date:  2006-06-05       Impact factor: 11.205

2.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

3.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

4.  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

5.  Asymmetric Friedel-crafts reaction of indoles with imines by an organic catalyst.

Authors:  Yong-Qiang Wang; Jun Song; Ran Hong; Hongming Li; Li Deng
Journal:  J Am Chem Soc       Date:  2006-06-28       Impact factor: 15.419

6.  A simple one-pot 2-step N-1-alkylation of indoles with α-iminoketones toward the expeditious 3-step synthesis of N-1-quinoxaline-indoles.

Authors:  Guillermo Martinez-Ariza; Muhammad Ayaz; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2013-12-04       Impact factor: 2.415

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.  Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

Authors:  Ryuji Hayashi; Gregory R Cook
Journal:  Org Lett       Date:  2007-03-09       Impact factor: 6.005

Review 9.  Isatin and its derivatives: a survey of recent syntheses, reactions, and applications.

Authors:  Rita Kakkar
Journal:  Medchemcomm       Date:  2019-01-15       Impact factor: 3.597

10.  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

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