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Structure elucidation of carbamoylo-β-lactam diastereoisomers by ROESY and NOESY experiments

Abstract

Recently we have focused in the problem of preparation of carbamoylo-β-lactams as a result of oxidative cyclization of malonyl enamides. In our experiments we obtain mixture of two main β-lactam products: as a result of subsequent elimination and a second as a product of substitution. All of the produced β-lactams have trans configuration what was confirmed by 1H coupling constants. However id should be stressed that in the case of substitution product, a new chiral center is generated, leading to formation of two pair of diastereoisomers.For elucidate their structures we used ROESY and NOESY experiments. Correlations between β-lactam protons and a methyl group allowed to assign structures of pairs of diastereisomers.

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Category:
Other
Type:
supllement, wydanie specjalne, dodatek
Published in:
Acta Biochimica Polonica no. 58,
ISSN: 0001-527X
Title of issue:
Acta Biochimica Polonica.
Language:
English
Publication year:
2011
Bibliographic description:
Punda P., Janikowska K., Makowiec S.: Structure elucidation of carbamoylo-β-lactam diastereoisomers by ROESY and NOESY experiments// Acta Biochimica Polonica. -Vol. 58., nr. Suppl. 4 (2011),
Verified by:
Gdańsk University of Technology

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