Beilstein J. Org. Chem.2011,7, 759–766, doi:10.3762/bjoc.7.86
explored as the enantiomerically pure amine. In the event 4a was generated after aza-Michaeladdition as a mixture of two stereoisomers, without any obvious diastereoisomeric bias (1:1, 0% de) as judged by both 1H and 19F NMR. β-Lactam ring closure, using thionyl chloride and triethylamine gave the N
is reported which took advantage of an aza-Michaeladdition between (S)-α-(p-methoxyphenyl)ethylamine (3b) and α-(trifluoromethyl)acrylic acid (2). Cyclisation and then chromatographic resolution of the β-lactam diastereoisomers 5b, followed by deprotection with ceric ammonium nitrate generated the β
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Graphical Abstract
Figure 1:
Enantiomers of α-(trifluoromethyl)-β-lactam (1).