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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1721-1737

Oxazoline-N-oxide mediated asymmetric cycloadditions. Recent progress in the stereo-selective syntheses of β-lactones and β-lactams

O. Dirat, C. Kouklovsky, M. Mauduit and Y. Langlois

Laboratoire de Synthése des Substances Naturelles, associé au CNRS, Université de Paris-sud, 91405, Orsay, France

Abstract: Camphor-derived oxazoline-N-oxides are versatile dipoles in a new kind of asymmetric [2+3] cycloadditions. Recent applications of this methodology allowed the stereoselective syntheses of several b-lactones natural products such as 1233A and tetrahydrolipstatine. Two formal syntheses of b-lactams antibiotics, b-methyl thienamycin and carpetimycin A, have also been achieved using this type of cycloaddition.