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

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 c...

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Detalles Bibliográficos
Autores principales: Jurčík, Václav, Slawin, Alexandra M Z, O'Hagan, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135179/
https://www.ncbi.nlm.nih.gov/pubmed/21804871
http://dx.doi.org/10.3762/bjoc.7.86
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author Jurčík, Václav
Slawin, Alexandra M Z
O'Hagan, David
author_facet Jurčík, Václav
Slawin, Alexandra M Z
O'Hagan, David
author_sort Jurčík, Václav
collection PubMed
description 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 (1)H and (19)F NMR correlation to the individual diastereoisomers of 5a and 5b.
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spelling pubmed-31351792011-07-29 Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam Jurčík, Václav Slawin, Alexandra M Z O'Hagan, David Beilstein J Org Chem Full Research Paper 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 (1)H and (19)F NMR correlation to the individual diastereoisomers of 5a and 5b. Beilstein-Institut 2011-06-06 /pmc/articles/PMC3135179/ /pubmed/21804871 http://dx.doi.org/10.3762/bjoc.7.86 Text en Copyright © 2011, Jurčík et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Jurčík, Václav
Slawin, Alexandra M Z
O'Hagan, David
Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
title Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
title_full Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
title_fullStr Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
title_full_unstemmed Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
title_short Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
title_sort single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135179/
https://www.ncbi.nlm.nih.gov/pubmed/21804871
http://dx.doi.org/10.3762/bjoc.7.86
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