The Preparation Of Aziridines Via Reaction Of Vicinal Amino Alcohols With Perfluorosulfonvl Fluoride

The versatility and high reactivity of the aziridines make them attractive intermediates for the synthesis of various types of organic molecules.such as chiral amines,amino acids,amino alcohols.alkaloids,B-lactamics.Moreover,aziridines have been utilized as ligands in the chiral synthesis. A number of synthetic aziridines have found biological applications as antitumor agents,antibiotics,and as enzyme inhibitors. Several naturally occurring aziridines have been shown to exhibit antibiotic and antitumor activity.To dates.a variety of methods for the preparation of aziridines have been reported. In recent years.we have been devoting our efforts towards the synthesis of aziridines and made some achievements in this project.This work contained the following three aspects:1,the preparation of aziridines and nucleophilic ring opening reaction of aziridines were reviewed.2,the reaction of N-tolylsulfony protected vicinal amino alcohols with perfuloro butanesulfonyl fluoride in the presence of triethylamine or1,8-diazabicyclo(5,4,0) undec-7-ene (DBU) as base was described in detail. Thus, an efficient one-step synthesis of aziridines via intromolecular nucleophilic substitution of vicinal amino alcohols with perfluorosulforyl fluoride under room temperature was developed. This protocol has the advantages of readily availability of starting materials,mild conditions and easy work-upprocedure.etc.So it can be used in the preparation of aziridines as an alternative methodology.3,We proposed a reasonable mechanism based on the experimental results.