Single enantiomer synthesis of alpha-(trifluoromethyl)-beta-lactam
Abstract
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.
Citation
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 . https://doi.org/10.3762/bjoc.7.86
Publication
Beilstein Journal of Organic Chemistry
Status
Peer reviewed
ISSN
1860-5397Type
Journal article
Collections
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