Andrews, Giles A. Brown, J. Charmant, T. Peakman, Arlene Rebello, K. E. Walsh, T. Gallagher, N. Hales
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Aldehydes and Ketones as Dipolarophiles. Application to the Synthesis of Oxapenams
2-Substituted (6a–e) and 2, 2-disubstituted oxapenams (6f–g) are obtained in one step by thermolysis of the β-lactam-based oxazolidinone 4 in the presence of aldehydes and reactive ketones respectively; the C(6)-substituted oxazolidinone variant 7 reacts with hexafluoroacetone to give the enantiomerically pure oxapenam 8.
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