Tetrahedron Letters p. 3787 - 3790 (1986)
Update date:2022-07-29
Topics:
Davies, Stephen G.
Dordor-Hedgecock, Isabelle M.
Sutton, Kevin H.
Walker, Jonathan C.
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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