Homoallylic amines are useful synthetic intermediates, but the most convenient preparation – allylation of imines – is less well developed than the allylation of aldehydes. Imines can be challenging to work with because they are less electrophilic than aldehydes and are prone to hydrolysis. We have found that bench-stable α-amido sulfones are useful imine alternatives for nickel-catalyzed allylation with allylic acetates. The conditions work with a variety of substituted sulfones, and the use of substituted allylic acetates generally leads to high regioselectivity and diastereoselectivity to afford the branched products.

Nickel-catalyzed allylation of imines generated in situ from α-amido sulfones

250th National Meeting (2015)

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