Opening of a vinyl aziridine with p-toluenesulfonamide under TBAF catalysis: synthesis of 3,4-diamino-3,4-dideoxy-l-chiro-inositol

3,4-Diamino-3,4-dideoxy-l-chiro-inositol has been prepared from bromobenzene by a chemoenzymatic approach. The key chemical step was a tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening employing p-toluenesulfonamide as a nucleophile, establishing the 1,2-trans relationship of the amino groups.