Ketones carbon-nitrogen double reduction

Many aldehydes (RCHO) and ketones (R2CO) are converted into amines by reductive amination reduction in the presence of ammonia. Reduction can be accomplished catalytically or by use of sodium cyanohydridoboratc, NaBHjCN. Reaction involves reduction of an intermediate compound (an imine RCH NH or R2C NH) that contains a carbon-nitrogen double bond. 

In 1999 [22] and 2001 [23], Matsumura and co-workers reported the first examples of stereoselective hydrosilylation with HSiCla and (5)-proline derivatives as effective activators. These works can be considered as milestones for the asymmetric reduction of ketones and imines using HSiCla as reducing agent and paved the road to the synthesis of other related systems. Since then, considerable efforts have been devoted to the development of efficient catalysts for the reduction of carbon-nitrogen double bonds, and remarkable progress has been made. 

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