Abstract
The high syn selectivity (e.g., synlanti ⩾ 83:17) observed in epoxidation of the torsionally and sterically unbiased 5,6-cis,exo-disubstitutedbicyclo[2.2.2]oct-2-enes (bearing electron withdrawing groups) progressively decreases on going to dihydroxylation and 1,3-dipolar cycloadditions, with practically no selectivity in the case of nitrones and dominance of anti attack in the reactions of diazomethane (synlanti ⩽ 32:68), in contrast with predictions based on Cieplak's theory.
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