Tandem asymmetric conjugate addition-silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications

Article Article scientifique Lettre Tandem asymmetric conjugate addition-silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications eng 2002 author Knopff Oliver 134162 author Alexakis Alexandre 123950 3835-3837 10.1021/ol026644o 1523-7052 The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCl and NEt3. These enantiomerically enriched silyl enol ethers were submitted to four synthetic transformations to show their synthetic utility. The zinc enolates obtained from acyclic enones were found to be configurationally stable, as shown by the stereochemistry of the silyl enol ethers. Dewey 540 36 Département de chimie organique 141 false Organic letters 4 22 45a1c2b2-8eb6-4a41-8a43-74b110368930 Article (Published version) Restricted file1.pdf 75841 application/pdf Vignette Public file2.gif 17508 image/gif restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Tandem asymmetric conjugate addition-silylation of enantiomerically enriched zinc enolates. Synthetic importance and mechanistic implications	Organic letters			2002	680	0

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Knopff, Oliver