Allenes are intriguing and under-utilized precursors for oxidative transformations.  Our group has been particularly interested in the development of highly regio-, chemo- and stereocontrolled allene amination methods that produce bicyclic methyleneaziridines and allenic amines with broad substrate scope.  The transfer of the axial chirality of the allene to point chirality in the products with excellent fidelity permits ready access to these reactive scaffolds in high enantioselectivity.   This talk will describe the many ways in which bicyclic methyleneaziridines can be rapidly elaborated to stereochemically complex and densely functionalized amine motifs.  The utility of this allene aziridination strategy for the construction of bioactive aminocyclitols and 'hybrid' anthracycline anti-tumor agents will also be discussed.

Allenes as underutilized functional groups for reaction discovery

248th National Meeting (2014)

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