doi: 10.1055/s-0029-1219198.
Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst
Affiliations
- PMID: 20717504
- PMCID: PMC2922060
- DOI: 10.1055/s-0029-1219198
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Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst
Synlett.
.
Abstract
A novel fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst is prepared. The catalyst shows good activity and enantioselectivity for direct α-chlorination of aldehydes using N-chlorosuccinimide (NCS) as the chlorine source. It can be recovered from the reaction mixture by fluorous solid-phase extraction with excellent purity for direct reuse.
Figures
Plausible transition state of the chlorination reaction catalyzed by catalyst 1.
Preparation of fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst 1.
Catalyst recycling experiment.
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