Spirocyclic oxindoles are important scaffolds found in many natural products and pharmaceutical lead compounds, and their potency in biological systems is often dependent on the absolute configuration of the 3,3'-spirocyclic center. This presentation will discuss several recently developed catalytic methods for accessing spirooxindoles in excellent yields with high regio- and stereoselectivity. For example, we will discuss the enantioselective synthesis of spirocyclic tetrahydro-�-carbolines (spiroindolones), which represent a core structure found in the anti-malarial lead compound NITD609. A comparison of chiral Lewis acids and chiral BINOL-derived phosphoric acids as catalysts for this reaction will be presented.  In addition, we will discuss the regio- and stereoselective synthesis of spirooxindole oxazolines catalyzed by various Lewis acids.  Mechanistic details and computational studies for the stereo- and regiocontrol of both reactions will also be discussed.

Enantioselective synthesis of spiroindolones

243rd National Meeting (2012)

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