Synthesis of Functionalized Spirooxindole Polycycles: Use of Cyclic 1,3-Diones as Reactants or as Condition-Tuning Molecules

Abstract This account describes the strategies for synthesis of functionalized spirooxindole polycycles, including enantiomerically enriched forms, that we have developed and reported. The syntheses these complex molecules were accomplished in a few steps starting from relatively simple oxindole derivatives other reactants. Organocatalytic reactions involved kinetic resolution or dynamic transformation led to formation products with high diastereo- and/or enantioselectivities. Cyclic 1,3-diones, such as 1,3-cyclohexanedione, used reactants provide two reaction sites construction polycyclic ring systems. To tune conditions, 2-methyl-1,3-cyclohexanedione was employed. methods enabled polycycles bearing up seven stereogenic centers, will be useful potentially bioactive molecules. 1 Introduction 2 Formal (4+1) Cycloaddition Enantioselective Michael/Henry Cascade Reactions 3 Dynamic Stereoselective Aldol/Oxacyclization 4 Kinetic Asymmetric Transformation: Diastereo- Enantioconvergent 5 Dimerization 6 Conclusion