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The stereochemical outcomes of the conjugate addition reactions of 2‐acetylindole enolates to the unsaturated phenylglycinol‐derived oxazolopiperidone lactams 1a–f have been studied. After reduction of the 2‐acylindole carbonyl group, the Michael adduct cis‐6 underwent a Lewis acid‐promoted intramolecular α‐amidoalkylation, leading enantioselectively to the tetracyclic ring system of the indole alkaloid...
Optically active 5-substituted pyrrolidin-2-ones underwent conjugate addition to nitroalkenes to give the corresponding adducts in a diastereoselective manner. The presence of 18-crown-6 was crucial to achieve good stereoselective addition. Addition of 6-substituted piperidin-2-ones also gave the corresponding adduct in a stereoselective manner. The adduct was readily converted into a bicyclic lactam...
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