C-3 Selective Ring Opening of 2,3-Aziridino Alcohols and their Derivatives with Nucleophiles in the Presence of β-Cyclodextrin in Water

Abstract

For the first time a mild and efficient procedure has been developed for the C-3 selective ring opening, under biomimetic conditions, of 2,3-aziridino alcohols and their derivatives with nucleophiles such as aromatic thiols and amines catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding β-amino sulfides and diamines with high regioselectivity in impressive yields. The use of cyclodextrin precludes the use of either acid or base and the catalyst can be recovered and reused.