Highly Stereoselective Allylation of Hydrazones

While there are some examples of allyl indium additions to imines, there are no generally good ways to do this and control the stereochemistry. We have found that chiral hydrazones are excellent acceptors for allyl indium. Reactions proceed with aromatic and aliphatic hydrazones to afford homoallylic amines with extremely high levels of diastereoselectivity. We have reported the first catalytic enantioselective variant of this reaction.