OUR JOURNEY WITH AZIRIDINE, AZIRINE AND 4-HYDROXYCOUMARIN

Abstract

We have observed that the allylic zinc halide under identical reaction conditions acts in different modes for different electrophiles. For Ts-aziridines the halide part of the allylic halide has been introduced as a nucleophile and for the carbonyl compounds the simple allylation reaction occurred. To the best of our knowledge this is the first report where the allylic zinc halide is the source of halide as nucleophile.1 In another reaction of aziridine an efficient and new approach has been developed to synthesize bis(β, β′-dialkoxy carbonyl) derivatives through the reaction between N-tosylaziridines and malonate esters under ambient air using tBuOK in DMSO solvent. This reaction offers a broad substrate scope, metal-free synthesis, excellent regioselectivity, easily accessible reactants, and simple operation. A gram-scale synthesis demonstrates the potential applications of the present method.