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Synfacts 2008(12): 1314-1314
DOI: 10.1055/s-0028-1083595
DOI: 10.1055/s-0028-1083595
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New YorkVersatile Crossed-Claisen Rearrangement by Soft Enolization of Thioesters
Contributor(s):Paul Knochel, Andreas J. WagnerG. Zhou, D. Lim, D. M. Coltart*
Duke University, Durham, USA
Direct Carbon-Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002
Org. Lett. 2008, 10: 3809-3812
Duke University, Durham, USA
Direct Carbon-Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002
Org. Lett. 2008, 10: 3809-3812
Further Information
Publication History
Publication Date:
20 November 2008 (online)
Key words
Claisen rearrangement - thioesters - enolization
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.
Comment
The utility of this carbon-carbon bond-forming method is shown through the synthesis of the PI3-K inhibitor LY294002. Conveniently, untreated reagent-grade solvents were used and the reactions were carried out in air.