Single enantiomer synthesis of alpha-(trifluoromethyl)-beta-lactam
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The first synthesis of alpha-(trifluoromethyl)-beta-lactam ((S)-1) is reported. The route starts from alpha-(trifluoromethyl)acrylic acid (2). Conjugate addition of alpha-(p-methoxyphenyl)ethylamine ((S)-3b), generated an addition adduct 4b which was cyclised to beta-lactam 5b. Separation of the diastereoisomers by chromatography gave ((alpha S,3S)-5b). N-Debenzylation afforded the desired alpha-(trifluoromethyl)-beta-lactam ((S)-1). The absolute stereochemistry of diastereoisomers 5 was determined by X-ray crystallographic determination of a close structural analogue, (alpha S,3S)-5c, and then H-1 and F-19 NMR correlation to the individual diastereoisomers of 5a and 5b.
Jurcik , V , Slawin , A M Z & O'Hagan , D 2011 , ' Single enantiomer synthesis of alpha-(trifluoromethyl)-beta-lactam ' Beilstein Journal of Organic Chemistry , vol 7 , pp. 759-766 . DOI: 10.3762/bjoc.7.86
Beilstein Journal of Organic Chemistry
© 2011 Jurčík et al; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://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: (http://www.beilstein-journals.org/bjoc)
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