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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)]

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-(-)-ac...

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Publication status:
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Journal:
TETRAHEDRON LETTERS More from this journal
Volume:
27
Issue:
32
Pages:
3787-3790
Publication date:
1986-01-01
DOI:
ISSN:
0040-4039
Language:
English
Pubs id:
pubs:110826
UUID:
uuid:a950d73c-5527-4c8d-96e1-909418a04ba2
Local pid:
pubs:110826
Source identifiers:
110826
Deposit date:
2012-12-19

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