4.8 Article

Polystyrene-Supported TRIP: A Highly Recyclable Catalyst for Batch and Flow Enantioselective Allylation of Aldehydes

Journal

ACS CATALYSIS
Volume 6, Issue 11, Pages 7647-7651

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02621

Keywords

enantioselective catalysis; chiral phosphoric acids; polystyrene-supported catalysts; flow chemistry; organocatalysis

Funding

  1. Institute of Chemical Research of Catalonia (ICIQ) Foundation
  2. MINECO [CTQ2015-69136-R]
  3. DEC Generalitat de Catalunya [2014SGR827]

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The widely applicable TRIP phosphoric acid catalyst has been immobilized on polystyrene using a copolymerization-based strategy. The resin (PS-TRIP) has proven to be highly active and enantioselective in the asymmetric allylboration of aldehydes. Moreover, it has shown to be extremely robust, as it can be reused for 18 times, after which it still retained its activity. Lastly, to further prove the benefits of the immobilization, a continuous flow experiment spanning 28 h has been carried out with very high yields and ee's.

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