The asymmetric synthesis of β-lactams. Stereocontrolled asymmetric tandem Michael additions and alkylations of α,β-unsaturated acyl ligands bound to the chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]

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Abstract

Michael addition of lithium benzylamide to the enantiomerically pure (S)-E-crotonyl complex of [(η5-C5H5)Fe(CO)(PPh3)] followed by trapping of the resultant enolate with methyl iodide or methanol occurs with high diastereoselectivity and gives after decomplexation the essentially optically pure (3R), (4S)-(−)-3,4-dimethyl- and (4S)-(−)-4-methyl-N-benzyl-β-lactams respectively. Similarly, tandem addition of lithium benzylamide and methylation of the corresponding enantiomerically pure R-(−)-acryloyl complex gave after decomplexation the essentially optically pure (3S)-(−)-3-methyl-N-benzyl-β-lactam.

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