| Abstract
| - Metal-mediated carbonyl allylation, allenylation, and propargylation of optically pure azetidine-2,3-diones were investigated in both anhydrous and aqueous environments. Different metalspromoters showed varied regioselectivities on product formation during allenylation/propargylationreactions of the keto-β-lactams. The stereochemistry of the new C3-substituted C3-hydroxyquaternary center was controlled by placing a chiral auxiliary at C4. In this way, the coupling ofazetidine-2,3-diones with a variety of propenyl-, propynyl-, and allenylmetal reagents offers aconvenient asymmetric entry to potentially bioactive 3-substituted 3-hydroxy-β-lactams.
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