Catalytic asymmetric Claisen rearrangement of unactivated allyl vinyl ethers.
Nearly a century after their original discovery, catalyzed enantioselective variants of the venerable Claisen rearrangement remain relatively rare. We have discovered a cooperative transition metal-Lewis acid cocatalyst system that affects highly enantio- and diastereoselective examples of archetypical Claisen rearrangements. The catalyzed rearrangements proceed using an easily prepared enantioenriched transition metal catalyst and a commercially available Lewis acid cocatalyst at ambient temperature in common solvents.
Geherty
Maryll E
ME
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Dura
Robert D
RD
Nelson
Scott G
SG
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D000447:Aldehydes; D009942:Organometallic Compounds; D014753:Vinyl Compounds; C100195:vinyl ether; D012428:Ruthenium