The first synthesis of α-(trifluoromethyl)-β-lactam ((<i>S</i>)-<b>1</b>) is reported. The route starts from α-(trifluoromethyl)acrylic acid (<b>2</b>). Conjugate addition of α-(<i>p</i>-methoxyphenyl)ethylamine ((<i>S</i>)-<b>3b</b>), generated an addition adduct <b>4b</b> which was cyclised to β-lactam <b>5b</b>. Separation of the diastereoisomers by chromatography gave ((α<i>S,</i>3<i>S</i>)-<b>5b</b>). N-Debenzylation afforded the desired α-(trifluoromethyl)-β-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, (α<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>
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