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Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands

Bourgeois, Frederic and Medlock, Jonathan A. and Bonrath, Werner and Sparr, Christof . (2020) Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands. Organic Letters, 22 (1). pp. 110-115.

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Official URL: https://edoc.unibas.ch/74210/

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Abstract

A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting materials. By capitalizing from the capacity of prolineamides to act as both an organocatalyst and a transfer hydrogenation ligand, catalyst repurposing allowed the development of an operationally simple, economic, and efficient sequential catalysis approach.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr)
UniBasel Contributors:Sparr, Christof and Bourgeois, Frederic
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:1523-7060
e-ISSN:1523-7052
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
Last Modified:28 Jan 2020 10:12
Deposited On:21 Jan 2020 10:35

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