THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - STEREOCONTROLLED ASYMMETRIC TANDEM MICHAEL ADDITIONS AND ALKYLATIONS OF ALPHA,BETA-UNSATURATED ACYL LIGANDS BOUND TO THE CHIRAL AUXILIARY [BETA-C5H5)FE(CO)(PPH3)]

Journal article

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.

Authors: Davies, S; Dordorhedgecock, I; Sutton, K; Walker, J

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 27
• Issue: 32
• Pages: 3787-3790
• Publication date: 1986-01-01
• DOI: 10.1016/S0040-4039(00)83881-2
• ISSN: 0040-4039
• Language: English