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Asymmetric synthesis of beta-lactams and pseudopeptides via stereoselective conjugate additions of lithium (alpha-methylbenzyl)-allylamide to alpha,beta-unsaturated iron acyl complexes

Abstract:

Lithium (a-methylbenzyl)allylamide 2 undergoes stereoselective conjugate additions to u,β-unsaturated iron acyl complexes 3a-c to afford β-amino iron acyl adducts 5a-c and 6a-c. These adducts may be deallylated smoothly using palladium(O) catalysis providing the corresponding homochira! secondary amines 7a-c which, upon oxidative decomplexation with bromine or //-bromosuccinimide, undergo direct β-lactam ring formation. The diastereoselectivity for the conjugate addition to 3a may be further ...

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Publication status:
Published

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Publisher copy:
10.1039/a906633k

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Garrido, NM More by this author
Shilvock, JP More by this author
Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
21
Pages:
3105-3110
Publication date:
1999-11-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:9941cb08-a2f7-4f88-816e-ec223163d0bd
Source identifiers:
110610
Local pid:
pubs:110610
Language:
English

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