ONE STEP SYNTHESIS OF AZIRIDINES BY THE MICHAEL TYPE ADDITION OF FREE SULFIMIDES

Article abstract of DOI:10.1016/0040-4020(80)85027-7

The Michael type additions of diphenyl N-unsubstituted sulfimide (free sulfimide) to various electrophilic olefins were carried out.The reaction with cis- and trans-dibenzoylethylene, dimethylfumarate, dimethylmaleate, benzalacetophenone and benzalacetone gave mainly the corresponding trans-2-acylaziridines and trans-enaminoketones.However, phenyl vinyl sulfone or acrylonitrile afforded not the corresponding aziridine but diphenyl-N-2-cyano or N-2-phenylsulfonylethylsulfimide, a simple Michael adduct.When optically active (+)-(R)-o-methoxyphenylphenyl free sulfimide was treated with such an α,β-unsaturated carbonyl compound as benzalacetophenone, an optically active 2-acylaziridine, i.e., (-)-trans-2-benzoyl-3-phenylaziridine was obtained in ca 30percent optical purity and its absolute configuration was assigned as (2R,3S) upon chemical transformation to the configurationally known 2-phenyl-2-benzoylamino-1-ethanol or by comparing its CD spectrum with that of (1R,2R)-1-phenyl-2-benzoyl-cyclopropane.Meanwhile, (-)-(S)-o-methoxyphenylphenyl free sulfimide was found to react with benzalacetophenone to afford (+)-trans-2-benzoyl-3-phenylaziridine of 25percent optical purity.Effects of solvent and temperature on both the distribution of the products ratio and the optical yield were examined.