Diastereodivergent Synthesis of Enantiomerically Pure Homoallylic Amine Derivatives Containing Quaternary Carbon Stereocenters

Freedom of choice: Both enantiomers of free homoallylic amines with two stereogenic centers (including a quaternary center) can be prepared at will from vinyl copper intermediates derived from either a vinyl iodide or an alkyne (see examples; the sulfinyl group is cleaved readily under mild acidic conditions). In this one-pot strategy, zinc homologation of the vinyl copper species is followed by treatment with a sulfinylimine derivative.