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Organocatalytic Enantioselective Michael/Cyclization Domino Reaction between 3‑Amideoxindoles and α,β-Unsaturated Aldehydes: One-Pot Preparation of Chiral Spirocyclic Oxindole-γ-lactams

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journal contribution
posted on 13.03.2017, 00:00 by Peng Yang, Xiao Wang, Feng Chen, Zheng-Bing Zhang, Chao Chen, Lin Peng, Li-Xin Wang
The first organocatalytic enantioselective Michael/cyclization domino reaction between 3-amideoxindoles and α,β-unsaturated aldehydes is described. After sequential oxidation with pyridinium chlorochromate, a direct and one-pot preparation of highly sterically hindered spirocyclic oxindole-γ-lactams was achieved in 51–81% yields with 75–97% ee and ≤80/20 dr.