Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam

Beilstein Journal of Organic Chemistry. 2011;7(1):759-766 DOI 10.3762/bjoc.7.86

 

Journal Homepage

Journal Title: Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)

Publisher: Beilstein-Institut

LCC Subject Category: Science: Chemistry: Organic chemistry

Country of publisher: Germany

Language of fulltext: English

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AUTHORS

Václav Jurčík (EASTChem School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK)
Alexandra M. Z. Slawin (EASTChem School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK)
David O'Hagan (EASTChem School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK)

EDITORIAL INFORMATION

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Time From Submission to Publication: 17 weeks

 

Abstract | Full Text

The first synthesis of α-(trifluoromethyl)-β-lactam ((S)-1) is reported. The route starts from α-(trifluoromethyl)acrylic acid (2). Conjugate addition of α-(p-methoxyphenyl)ethylamine ((S)-3b), generated an addition adduct 4b which was cyclised to β-lactam 5b. Separation of the diastereoisomers by chromatography gave ((αS,3S)-5b). N-Debenzylation afforded the desired α-(trifluoromethyl)-β-lactam ((S)-1). The absolute stereochemistry of diastereoisomers 5 was determined by X-ray crystallographic determination of a close structural analogue, (αS,3S)-5c, and then 1H and 19F NMR correlation to the individual diastereoisomers of 5a and 5b.