Study On Asymmetric Synthesis Of Some Chiral Aziridine Devirations

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, aminoacids, amino alcohols, alkaloid,β-lactamic, polymers. Moreover, chiral aziridines have been utilized as ligands and auxiliaries in efficient asymmetric 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. Despite these interests, the methods for the synthesis of these compounds in enantiomerically pure form are rather limited. In this paper, some aziridines with new structure have been synthesized based on the patented applied prospects and the main results as follows: (1) chiral sythons for 5-menthyloxy-2-(5H)-furanone (3) and 3-bromo-2(5H) -furanone (5a) were synthesized via photochemical reaction, acetalization, bromine addition and elimination reaction for hydrogen bromide using furfural, a very cheap material. The synthesis of racemic 5-menthyloxy-2-(5H)-furanone (3) was conveniently achieved in good yield through acetalization of the resulting 5-hydroxy-2(5H)-furanone (2) in menthol under refluxing, which is easily obtained by the photooxidation of furfural. 5-menthyloxy-3-bromo-2(5H)-furanone 5a was easily prepared in four steps in good yield from furfural (1) on large scale.(2) 5-(R)-menthyloxy-butyrolacto[3,4-b]-2(S)-6(R)-1-N-alkyl-aziri-...