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Synlett 2010(3): 433-436  
DOI: 10.1055/s-0029-1219198
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Liang Wanga,c, Chun Cai*a, Dennis P. Curranb, Wei Zhang*c
a Chemical Engineering College, Nanjing University of Science & Technology, Nanjing 210094, P. R. of China
Fax: +86(25)84315030; e-Mail: c.cai@mail.njust.edu.cn;
b Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
c Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA 02125, USA
Fax: +1(617)2876030; e-Mail: wei2.zhang@umb.edu;
Further Information

Publication History

Received 21 October 2009
Publication Date:
15 January 2010 (online)

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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.

Key words

bifunctional organocatalyst - α-chlorination - α-chloroaldehyde - N-chlorosuccinimide (NCS) - fluorous catalyst - fluorous solid-phase extraction (F-SPE)

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Fluorous columns and products were purchased from Fluorous Technologies, Inc. D.P.C. owns an equity interest in this company.