Palladium-catalyzed [1,3]-O-to-C rearrangement of pyrans toward functionalized cyclohexanones.
Functionalized cyclohexanones are prepared from cyclic enol ethers via a Pd-catalyzed [1,3]-O-to-C rearrangement reaction. α-Arylketones are generated with excellent diastereocontrol when basic phosphine ligands are used. In contrast, a Lewis acid is required to promote the rearrangement of the alkyl-substituted enol ether systems.
Brioche
Julien C R
JC
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, United Kingdom.
Barker
Thomas A
TA
Whatrup
David J
DJ
Barker
Michael D
MD
Harrity
Joseph P A
JP
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
D003512:Cyclohexanones; D008024:Ligands; D011714:Pyrans; D010165:Palladium; D002244:Carbon; D010100:Oxygen