Polystyrene or Magnetic Nanoparticles as Support in Enantioselective Organocatalysis? A Case Study in Friedel–Crafts Chemistry

Polystyrene or Magnetic Nanoparticles as Support in Enantioselective Organocatalysis? A Case Study in Friedel–Crafts Chemistry

Heterogenized versions of the second-generation MacMillan imidazolidin-4-one are described for the first time. This versatile organocatalyst has been supported on 1% DVB Merrifield resin and Fe3O4 magnetic nanoparticles through a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. The resu...

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Veröffentlicht in:Organic letters 2016-04, Vol.18 (7), p.1602-1605
Hauptverfasser: Ranjbar, Sara, Riente, Paola, Rodríguez-Escrich, Carles, Yadav, Jagjit, Ramineni, Kishore, Pericàs, Miquel A
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container_end_page 1605
container_issue 7
container_start_page 1602
container_title Organic letters
container_volume 18
creator Ranjbar, Sara
Riente, Paola
Rodríguez-Escrich, Carles
Yadav, Jagjit
Ramineni, Kishore
Pericàs, Miquel A
description Heterogenized versions of the second-generation MacMillan imidazolidin-4-one are described for the first time. This versatile organocatalyst has been supported on 1% DVB Merrifield resin and Fe3O4 magnetic nanoparticles through a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. The resulting catalytic materials have been successfully applied to the asymmetric Friedel–Crafts alkylation of indoles with α,β-unsaturated aldehydes. While both catalytic systems can be easily recovered and admit repeated recycling, the polystyrene-based catalyst shows higher stability and provides better stereoselectivities.
doi_str_mv 10.1021/acs.orglett.6b00462
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title Polystyrene or Magnetic Nanoparticles as Support in Enantioselective Organocatalysis? A Case Study in Friedel–Crafts Chemistry
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