Highly Diastereoselective Reaction of α-Diazoesters with Aryl Alcohols and Isatin Imines: Rapid Access to Oxindole-Derived α-Alkoxy-β-amino Acid Derivatives with Two Adjacent Quaternary Carbon Centers

A stereoselective synthesis of oxindole-derived α-alkoxy-β-amino acid derivatives was achieved in high yield with excellent diastereoselectivity through the three-component reaction of methyl 2-diazoarylacetate, aryl alcohols, and isatin-derived ketimines by using Rh2(OAc)4 (1 mol-%) as the catalyst. The products are very useful for the synthesis of analogues of the gastrin receptor antagonist AG-041R, spirooxindolyl β-lactams, the oxindole-derived side chain of Taxol, and natural product cytoxazone and aminopyrrolo[2,3-b]indoline derivatives.

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