We report stereodivergent allylic substitutions with heteroarylacetates and heteroarylacetamides catalyzed synergistically by a metallacyclic iridium complex and a Lewis acidic copper complex. Through permutations of enantiomers of two chiral catalysts, all four possible stereoisomers of the products bearing two vicinal stereocenters are synthesized individually from the same set of starting materials under otherwise identical conditions with high diastereoselectivity and enantioselectivity. Mechanistic studies were performed to understand the stereoselectivity of the allylation reaction of the copper enolate.

Stereodivergent allylation of heteroarylacetates and heteroarylacetamides by synergistic iridium and copper catalysis

255th National Meeting (2018)

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