Structural characterization of an enantiomerically pure amino acid imidazolide and direct formation of the beta-lactam nucleus from an alpha-amino acid.
Org Lett
; 10(3): 369-72, 2008 Feb 07.
Article
em En
| MEDLINE
| ID: mdl-18181633
ABSTRACT
Decomposition of a diazo beta-ketoamide derived from N-trityl serine imidazolide and N-protected acetanilides provides, instead of the expected 3-acyloxindole product, an enantiomerically pure (EP) beta-lactam. The amino acid stereocenter is incorporated, the second chiral center is induced, and trityl protection of the beta-lactam ring is realized for the first time. The desired 3-acyloxindole is obtained from oxindole and Tr-Ser(OBn)-imidazole, the X-ray of which provides the first structural determination of an EP amino acid imidazolide.
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Coleções:
01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article