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Synthesis 2023; 55(15): 2361-2369
DOI: 10.1055/a-2085-5256
DOI: 10.1055/a-2085-5256
paper
Special Issue dedicated to Prof. David A. Evans
Asymmetric Transfer Hydrogenation of Heterocyclic Compounds in Continuous Flow Using an Immobilized Chiral Phosphoric Acid as the Catalyst
Autor*innen
These studies have been supported by the National Science Foundation (NSF) (Grant No. CHE-1955069).
This manuscript is dedicated to Professor David A. Evans.
Abstract
This manuscript describes transfer hydrogenation of bicyclic nitrogen-containing heterocyclic compounds using the immobilized chiral phosphoric acid catalyst (R)-PS-AdTRIP in batch and continuous flow. A significant improvement in enantioselectivities is achieved in continuous flow with a fluidized bed reactor packed with (R)-PS-AdTRIP when the flow rate is increased from 0.2 mL/min to 2.0–2.5 mL/min. The optimized continuous flow conditions consistently provide 4–6% ee higher selectivity than transfer hydrogenation in batch with 2 mol% of (R)-PS-AdTRIP, and are used to generate multiple chiral products with the same fluidized bed reactor.
Key words
transfer hydrogenation - chiral phosphoric acid - continuous flow - enantioselectivity - heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2085-5256.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 11. März 2023
Angenommen nach Revision: 03. Mai 2023
Accepted Manuscript online:
03. Mai 2023
Artikel online veröffentlicht:
29. Juni 2023
© 2023. Thieme. All rights reserved
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