Copper Hydride is a versatile reducing agent which allows for ligation of chiral ligands in order effect asymmetric reduction of pi-bonds. It has been broadly used for the asymmetric reduction of carbonyl compounds, imines, and conjugated alkenes, but it has not yet been applied to the reduction of strained heterocycles. This body of research focuses on the development of an asymmetric reduction of 2<i>H</i>-azirines to produce chiral aziridines. We screened several chiral ligand families (SEGPHOS, JOSIPHOS, GARPHOS), silicon-based hydride sources, and solvents to optimize yield and stereoselectivity.

Preparation of chiral aziridines through a copper-catalyzed asymmetric reduction of 2<i>H</i>-azirines

255th National Meeting (2018)

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Preparation of chiral aziridines through a copper-catalyzed asymmetric reduction of 2H-azirines