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Synthesis 2011(2): 281-286  
DOI: 10.1055/s-0030-1258359
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Organocatalytic α-Sulfenylation of Aldehydes and Ketones with Tetramethylthiuram Disulfide

Dieter Enders*, Andreas Rembiak, Jens X. Liebich
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
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Publikationsverlauf

Received 10 November 2010
Publikationsdatum:
10. Dezember 2010 (online)

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Abstract

The direct pyrrolidine-catalyzed α-sulfenylation of aldehydes and ketones with the commercially available, very cheap chemical tetramethylthiuram disulfide (thiram) is described. The dithiocarbamoyl derivatives are obtained in good to excellent yields (47-98%). In the case of α-substituted aldehydes the protocol allows the generation of quaternary stereocenters. The sensibility of the α-sulfenylated carbonyl compounds for racemization has been investigated.

Key words

organocatalysis - thiram - sulfenylation - dithiocarbamate - enamine

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