Reduction of a-Amino Ketimines

Organometallic Addition/Reduction Sequence on Chiral o -Aminonitriles 

Optically pure a-amino acids can be converted to 1,2-diamines by a route that involves the preliminary formation of N-protected a-aminonitriles through the intermediate amides. The addition of organometallic reagents to these a-aminonitriles gives a-amino ketimines, which are then reduced in situ to 1,2-diamines. However, this route has been scarcely applied to acychc a-aminonitriles. As a matter of fact, the sequential addition of methylmag- 

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Scheme 31 Auxiliary-induced diastereoselective reduction of a-amino ketimines...

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