A catalytic asymmetric Claisen rearrangement was recently developed utilizing a late transition metal/Lewis acid co-catalyst system.  Enantioenriched CpRu(II)+ complexesin conjunction with trivalent Lewis acids afford an effective catalyst for enantioselective Claisen rearrangements. These reactions proceed from structurally simple allyl vinyl ethers devoid of auxiliary functionality to assist substrate-catalyst association.  Reactions produce a-unsubstituted aldehyde products free of epimerization that commonly plagues the formation of enolizable a-chiral aldehydes. The products were obtained in high yields along with excellent enantioselectivities and diastereoselectivities.

Transition metal mediated catalytic asymmetric Claisen (CAC) rearrangment of unsubstituted allyl vinyl ethers

239th National Meeting (2010)

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