The direct, stereoselective functionalization of unreactive C�H bonds is of great interest from a synthetic standpoint. High-spin iron(II) dipyrrinato complexes are competent for direct C�H bond amination, converting linear alkyl azides to N-heterocycles in a catalytic fashion. Efforts directed towards rendering this transformation stereoselective led to the synthesis of a series of iron complexes bearing alkoxide or ortho-substituted phenoxide ligands. A reactivity assay revealed that an iron-phenoxide precatalyst is capable of furnishing 2,5-disubstituted pyrrolidines with high diastereocontrol as determined via 1H NMR and GC-MS.  Factors contributing to the diastereoselectivity will be discussed. Extending these principles to develop an enantioselective C�H bond amination catalyst variant will also be discussed.

Catalytic stereoselective C-H bond amination using iron dipyrromethene complexes

248th National Meeting (2014)

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