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Enantiopure 2-azetidinone-tethered alkynylaldehydes 1 react stereoselectively under mild conditions with N-methylhydroxylamine to yield products derived from either intramolecular reverse-Cope elimination or 1,3-dipolar cycloaddition, depending on both the length of the tether and the experimental conditions.
New asymmetric routes based on both Baylis-Hillman and allylation reactions of enantiopure 3-oxo-2-azetidinones are used for the highly stereoselective, efficient preparation of densely functionalized 3-substituted 3-hydroxy-β-lactams.
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