Literature DB >> 15783181

Highly enantioselective Friedel-Crafts alkylations of pyrroles and indoles with alpha'-hydroxy enones under Cu(II)-simple bis(oxazoline) catalysis.

Claudio Palomo1, Mikel Oiarbide, Bharat G Kardak, Jesús M García, Anthony Linden.   

Abstract

Remarkably high and regular enantioselectivities are obtained in Friedel-Crafts alkylation reactions involving alpha'-hydroxy enone templates and Cu(II)-bis(oxazoline) complexes as catalysts. The simple elaboration of adducts provides a route to enantioenriched aldehydes, carboxylic acids, and ketones containing the pyrrole and indole frameworks.

Entities:  

Year:  2005        PMID： 15783181     DOI： 10.1021/ja0423217

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 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.  Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors:  Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-23       Impact factor: 15.336

3.  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

4.  Alpha'-hydroxyenones as mechanistic probes and scope-expanding surrogates for alpha,beta-unsaturated aldehydes in N-heterocyclic carbene-catalyzed reactions.

Authors:  Pei-Chen Chiang; Michael Rommel; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2009-06-24       Impact factor: 15.419

5.  Development of a merged conjugate addition/oxidative coupling sequence. Application to the enantioselective total synthesis of metacycloprodigiosin and prodigiosin R1.

Authors:  Michael D Clift; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

6.  Exploiting the Chiral Ligands of Bis(imidazolinyl)- and Bis(oxazolinyl)thiophenes-Synthesis and Application in Cu-Catalyzed Friedel-Crafts Asymmetric Alkylation.

Authors:  Mohammad Shahidul Islam; Abdullah Saleh Alammari; Assem Barakat; Saeed Alshahrani; Matti Haukka; Abdullah Mohammed Al-Majid
Journal:  Molecules       Date:  2021-12-06       Impact factor: 4.411

7.  Lewis Acid-Catalyzed Enantioselective Friedel-Crafts Alkylation of Pyrrole in Water.

Authors:  Jianan Sun; Yang Gui; Yekai Huang; Jindong Li; Zhenggen Zha; Yu Yang; Zhiyong Wang
Journal:  ACS Omega       Date:  2020-05-11
  7 in total

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