Tetrabutylammonium bromide (TBAB) was found to be a highly effective catalyst at as low as 10 mol% for regioselective ringopening of a variety of N-tosylaziridines with various carboxylicacids to afford the corresponding ring-opening products (derived β-amino esters) in good to excellent yields and up to 100% regioselectivity in combination with DMF as the solvent.
NaHSO3-Promoted Ring Openings of N-Tosylaziridines and Epoxides with H2O
作者:Wen-Long Wei、Xing Li、Bin Ni、Hong-Hong Chang
DOI:10.3987/com-13-12885
日期:——
NaHSO3-oriented ring openings of a wide variety of N-tosylaziridines and epoxides with H2O under mild conditions in acetone was found to be a convenient and effective method, which provided the desired beta-aminoalcohols and beta-diols in good to excellent yields and with uniformly high regioselectivity.
KOH-catalyzed regioselective ring openings of N-tosylaziridines with malonates in acetone
A simple and efficient method has been developed which describes KOH-oriented catalytic regioselective ring-opening reactions of various N-tosylaziridines with malonates. In the presence of 20 mol% KOH, most N-tosylaziridines can smoothly react with malonates to give the corresponding products in good to excellent yields (up to 99%) and with good to excellent regioselectivity under mild experimental conditions. (c) 2012 Elsevier B.V. All rights reserved.