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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. © 1986.

Original publication

DOI

10.1016/S0040-4039(00)83881-2

Type

Journal article

Journal

Tetrahedron Letters

Publication Date

01/01/1986

Volume

27

Pages

3787 - 3790