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

• Václav Jurčík,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2011, 7, 759–766, doi:10.3762/bjoc.7.86

• Vaclav Jurcik Alexandra M. Z. Slawin David O'Hagan EASTChem School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK 10.3762/bjoc.7.86 Abstract The first synthesis of α-(trifluoromethyl)-β-lactam ((S)-1) is reported. The route

• ; organofluorine building blocks; α-(trifluoromethyl)-β-lactam; Introduction β-Lactams (azetidin-2-ones) have played a prominent role in medicinal chemistry and many structural variants have been prepared and elaborated [1]. Similarly, the CF3 group is an ubiquitous substituent in pharmaceutical research, where

• of α-(trifluoromethyl)-β-lactam (1) which allows access to its enantiomerically pure forms, (R)-1 and (S)-1 as illustrated in Figure 1. Results and Discussion The synthesis shown in Scheme 1 follows a strategy developed [14] for enantiomers of the methyl analogue of 1, and starts from α