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Enantioselective α-Chlorination of Aldehydes with Recyclable Fluorous (S)-Pyrrolidine-Thiourea Bifunctional Organocatalyst

Liang Wang, Chun Cai*, Dennis P. Curran, Wei Zhang

*Chemical Engineering College, Nanjing University of Science & Technology, Nanjing 210094, P. R. of China, Email:

L. Wang, C. Cai, D. P. Curran, W. Zhang, Synlett, 2010, 433-436.

DOI: 10.1055/s-0029-1219198

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A fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst shows good activity and enantioselectivity for direct α-chlorination of aldehydes using N-chlorosuccinimide (NCS) as the chlorine source. The catalyst can be recovered from the reaction mixture by fluorous solid-phase extraction with excellent purity for direct reuse.

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Key Words

α-chlorination, organocatalysis, α-chloroaldehydes, N-chlorosuccinimide (NCS), fluorous catalyst, fluorous solid-phase extraction (F-SPE)

ID: J60-Y2010-0410