Literature DB >> 23815365

Catalytic Friedel-Crafts reaction of aminocyclopropanes.

Florian de Nanteuil1, Joachim Loup, Jérôme Waser.   

Abstract

A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups and substitution patterns. In the case of C3-substituted indoles, C2 alkylation was observed. The reaction gives a rapid access to gamma amino acid derivatives present in numerous bioactive molecules.

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Year:  2013        PMID: 23815365     DOI: 10.1021/ol401616a

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors:  Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal:  European J Org Chem       Date:  2021-08-25

2.  Radical differentiation of two ester groups in unsymmetrical diazomalonates for highly asymmetric olefin cyclopropanation.

Authors:  Jingyi Wang; Jingjing Xie; Wan-Chen Cindy Lee; Duo-Sheng Wang; X Peter Zhang
Journal:  Chem Catal       Date:  2021-12-29

3.  Ring-Opening 1,3-Aminochalcogenation of Donor-Acceptor Cyclopropanes: A Three-Component Approach.

Authors:  André U Augustin; Peter G Jones; Daniel B Werz
Journal:  Chemistry       Date:  2019-08-07       Impact factor: 5.236

4.  Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides.

Authors:  Shiqun Xiang; Yinghua Li; Weibin Fan; Jiang Jin; Wei Zhang; Deguang Huang
Journal:  Front Chem       Date:  2021-01-29       Impact factor: 5.221

5.  BF3-OEt2 Catalyzed C3-Alkylation of Indole: Synthesis of Indolylsuccinimidesand Their Cytotoxicity Studies.

Authors:  Iqbal N Shaikh; Abdul Rahim; Shaikh Faazil; Syed Farooq Adil; Mohamed E Assal; Mohammad Rafe Hatshan
Journal:  Molecules       Date:  2021-04-11       Impact factor: 4.411

6.  Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Authors:  Vincent Pirenne; Emma G L Robert; Jerome Waser
Journal:  Chem Sci       Date:  2021-05-05       Impact factor: 9.825

7.  Cobalt-catalysed reductive C-H alkylation of indoles using carboxylic acids and molecular hydrogen.

Authors:  Jose R Cabrero-Antonino; Rosa Adam; Kathrin Junge; Matthias Beller
Journal:  Chem Sci       Date:  2017-07-26       Impact factor: 9.825

8.  Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates.

Authors:  Jan Wallbaum; Lennart K B Garve; Peter G Jones; Daniel B Werz
Journal:  Org Lett       Date:  2016-12-14       Impact factor: 6.005

Review 9.  Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

Authors:  Daniel B Werz; Akkattu T Biju
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336

10.  Brønsted Acid Catalyzed (4 + 2) Cyclocondensation of 3-Substituted Indoles with Donor-Acceptor Cyclopropanes.

Authors:  Alesandere Ortega; Uxue Uria; Tomás Tejero; Liher Prieto; Efraim Reyes; Pedro Merino; Jose L Vicario
Journal:  Org Lett       Date:  2021-03-09       Impact factor: 6.072

  10 in total

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