Literature DB >> 21561153

Enantioselective synthesis of highly substituted furans by a copper(II)-catalyzed cycloisomerization-indole addition reaction.

Vivek Rauniyar1, Z Jane Wang, Heather E Burks, F Dean Toste.   

Abstract

A catalytic enantioselective reaction based on a copper(II) catalyst strictly containing chiral anionic ligands is described. In the present work, copper(II)-phosphate catalyst promotes the intramolecular heterocyclization of 2-(1-alkynyl)-2-alkene-1-ones and facilitates high levels of enantioselectivity in the subsequent nucleophile attack. Mechanistic studies suggest that formation of a copper(II)-indole species is important for catalysis.

Entities:  

Year:  2011        PMID: 21561153     DOI: 10.1021/ja202959n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   16.383


  17 in total

1.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

3.  A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.

Authors:  Dillon H Miles; Joan Guasch; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

4.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

5.  Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Chirality       Date:  2013-11-07       Impact factor: 2.437

6.  Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

Authors:  Jean-François Brazeau; Suyan Zhang; Ignacio Colomer; Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

7.  Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis.

Authors:  Yugen Zhu; Wei He; Wei Wang; Chloe E Pitsch; Xiaotai Wang; Xiang Wang
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-23       Impact factor: 15.336

8.  Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors:  Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal:  Adv Synth Catal       Date:  2019-09-06       Impact factor: 5.837

9.  Gold(I)-Catalyzed Enantioselective Desymmetrization of 1,3-Diols through Intramolecular Hydroalkoxylation of Allenes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-30       Impact factor: 15.336

Review 10.  Asymmetric ion-pairing catalysis.

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

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