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

By David O'Hagan, Alexandra M. Z. Slawin and V&#225


The first synthesis of &#945;-(trifluoromethyl)-&#946;-lactam ((<i>S</i>)-<b>1</b>) is reported. The route starts from &#945;-(trifluoromethyl)acrylic acid (<b>2</b>). Conjugate addition of &#945;-(<i>p</i>-methoxyphenyl)ethylamine ((<i>S</i>)-<b>3b</b>), generated an addition adduct <b>4b</b> which was cyclised to &#946;-lactam <b>5b</b>. Separation of the diastereoisomers by chromatography gave ((&#945;<i>S,</i>3<i>S</i>)-<b>5b</b>). N-Debenzylation afforded the desired &#945;-(trifluoromethyl)-&#946;-lactam ((<i>S</i>)-<b>1</b>). The absolute stereochemistry of diastereoisomers <b>5</b> was determined by X-ray crystallographic determination of a close structural analogue, (&#945;<i>S,</i>3<i>S</i>)-<b>5c</b>, and then <sup>1</sup>H and <sup>19</sup>F NMR correlation to the individual diastereoisomers of <b>5a</b> and <b>5b</b>

Topics: enantiomeric resolution, organofluorine building blocks, &#945;-(trifluoromethyl)-&#946;-lactam, Organic chemistry, QD241-441, Chemistry, QD1-999, Science, Q, DOAJ:Organic Chemistry, DOAJ:Chemistry
Publisher: Beilstein-Institut
Year: 2011
DOI identifier: 10.3762/bjoc.7.86
OAI identifier: oai:doaj.org/article:3482c4bc4ccb4a0cad08b0e60cc5b8b5
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