Do aziridines require Lewis acids for cleavage with ionic nucleophiles?
作者:Alakesh Bisai、Ghanshyam Pandey、Manoj K Pandey、Vinod K Singh
DOI:10.1016/s0040-4039(03)01414-x
日期:2003.7
variety of activatedaziridines were cleaved by sodium azide and sodium cyanide in aqueous acetonitrile at reflux, in the absence of any Lewisacid, to provide ring-opened products in quantitative yields. However, the reaction was sluggish in the ring opening of unactivated aziridines with sodium azide where the yields could be increased by adding 50 mol% CuCl2·2H2O. The reaction was used to synthesize
Efficient Ring Opening of Aziridines with Carboxylic Acids
作者:Manoj Kumar、Shikha Gandhi、Swinderjeet Singh Kalra、Vinod K. Singh
DOI:10.1080/00397910801928723
日期:2008.4.1
Abstract An efficient ring cleavage of aziridines with acids has been studied in the absence of any catalyst. The hydrolysis of the products, amino esters, leads to the corresponding amino alcohols. The reaction has been extended to chiral cycloalkyl aziridines, leading to the formation of diastereomers. After separation, these diastereomers have been converted to optically pure amino alcohols in two
The aminolysis of meso-N-phenyl aziridines is efficiently catalyzed with just 1 mol% of Sc(OTf)3 and furnishes valuable 1,2-diamines in good to excellent yields.