Resolved, chiral amines attract the attention of synthetic chemists because they are a prevalent functional group in a wide array of optically active pharmaceuticals, and they are used as chiral resolving agents as well as chiral auxiliaries for asymmetric transformations. During the past few decades, late transition metal catalyzed asymmetric hydrogenation has become a popular synthetic approach for obtaining enantiopure amines. However, despite good selectivity, reactions of this type are usually costly and hazardous due to the use of expensive transition metals and molecular hydrogen. This work describes efforts towards a reliable system for the synthesis of chiral amines via zirconium or hafnium mediated asymmetric reductive hydrogenation of the prochiral ketoimine substrates (E)-N-(α-methylbenzylidene)benzylamine and (E)-acetophenone O-diphenylphosphoryl oxime showing high conversion and varying stereoselectivity.

Synthesis of chiral amines via early transition metal mediated asymmetric reductive hydrogenation of prochiral imines

255th National Meeting (2018)

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