The alumina promoted 6-exo-trig intramolecular nitroaldol cyclization described proceeds in a highly diastereoselective manner via a proposed chelation controlled chair-like transition state, the major diastereomer having the correct relative configuration at three stereocentres as observed in the pancratistatin series of antitumor agents, in contrast to prior literature cyclization methods.
J. McNulty and R. Mo, Chem. Commun., 1998, 933 DOI: 10.1039/A800097B
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