A simple and versatile re-catalyzed Meyer-Schuster rearrangement of propargylic alcohols to alpha,beta-unsaturated carbonyl compounds.
Rhenium does the job! A readily available rhenium complex efficiently catalyzed the direct Meyer-Schuster-like rearrangement of different alkyl- and aryl-substituted propargylic secondary and tertiary alcohols to the corresponding alpha,beta-unsaturated compounds, which were produced with virtually complete E stereoselectivity. The reaction proceeded under neutral conditions and no racemization of potentially enolizable stereocenters was observed.
Stefanoni
Massimo
M
Dipartimento di Chimica Organica, Università di Pavia, Via Taramelli 10, Pavia, Italy.
Luparia
Marco
M
Porta
Alessio
A
Zanoni
Giuseppe
G
Vidari
Giovanni
G
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D007659:Ketones; D020005:Propanols; C028255:propargyl alcohol