The synthesis of chiral amines is of great interest in the pharmaceutical industry, accordingly there are a vast amount of syntheses that produce enantioenriched amines. However, most synthesis rely on either classical resolution techniques or chiral auxiliary based approaches leading to either waste of material or requires further chemical transformations. Asymmetric transfer hydrogenation (ATH) of imines on the other hand is both an operationally simple and efficient alternative to hydrogenations leading directly to the desired chiral amine. Although the ATH reduction of prochiral carbonyl compounds to the corresponding chiral alcohols is a well established and frequently used reaction with a wide substrate scope the current methodologies for the corresponding imines on the other hand are almost exclusively restricted to the use of activated (i.e. N-aryl, N-phosphinyl and N-sufonyl ) or conformationally restricted (cyclic) imines.   We have investigated and identified catalytic systems that are able to reduce acyclic non-activated ketimines in good to excellent yields and with enantioselectivities ranging from 89 to > 99 % ee.

Development of an efficient metal catalyzed asymmetric reductive amination

248th National Meeting (2014)

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