Ring Opening of 1,1’-Sulfonyl Bis-Aziridines Derived from L-Amino Acids and DFT Study of the Affinity Toward Different Nucleophiles

Abstract

: We describe herein the ring-opening reaction of chiral 1,1’-sulfonyl bis-aziridines with various neutral and anionic nucleophiles, including benzylamine, piperidine, acetate, allyl thiolate, cyanide anion, and sodium ethoxide. These reactions afforded bis-opened or/and mono-opened compounds via a regioselective attack on the non-substituted methylene of aziridine ring. The structures of the products were confirmed based on spectral analysis (IR, 1H NMR, and 13C NMR). A theoretical study involving density functional theory (DFT) was used to rationalize the region-selective ring-opening of starting bis-aziridines.