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Synfacts 2008(12): 1314-1314  
DOI: 10.1055/s-0028-1083595
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Versatile Crossed-Claisen Rearrangement by Soft Enolization of Thioesters

Contributor(s): Paul Knochel, Andreas J. Wagner
G. Zhou, D. Lim, D. M. Coltart*
Duke University, Durham, USA
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Publikationsverlauf

Publikationsdatum:
20. November 2008 (online)

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Significance

The chemoselective acylation of thioesters by N-acylbenzotriazoles on treatment with MgBr2˙OEt2 and DIPEA gives β-keto thioesters which are stable synthetic equivalents of β-keto acids and can smoothly be converted into esters, amides and diketones under mild conditions.