Oxazoline-N-oxide mediated asymmetric cycloadditions. Recent
progress in the stereo-selective syntheses of b-lactones
and b-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.
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
** Corresponding author
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