Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids

We report the use of bifunctional inputs (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. The study of the reaction scope reveals the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini scaffold -the α-carboxamido lactone- to an atypical product, an α-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis.

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