Twenty five years after Araki and Butsugan reported the first indium-mediated allylation reaction in water, our fundamental understanding of the nature of the organometallic reagent in this process remains murky. The recognition that a sesquihalide complex may be important for efficient allylation of carbonyls has resulted in the paradigm that a 3:2 ratio of allyl halide and indium metal, respectively, is required. Certainly stoichiometric amount of indium, at a minimum, is thought to be necessary. This has significant implications in the catalytic enantioselective indium-mediated allylation of alpha-ketoamides. We have discovered the stoichiometry of the indium metal has a remarkable impact on enantioselectivity of the reaction. Our recent discoveries and mechanistic insight we have gained will be presented.

New paradigm in enantioselective In-mediated allylation

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.