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.

Graphical abstractKOH-catalyzed regioselective ring-opening reactions of various N-tosylaziridines with malonates have been developed. In the presence of 20 mol% KOH, most N-tosylaziridines can smoothly react with malonates to give the corresponding products in good yields and with good regioselectivity under mild conditions.Figure optionsDownload full-size imageDownload high-quality image (123 K)Download as PowerPoint slideHighlights► This manuscript reported inorganic base-catalyzed ring-opening reactions of N-tosylaziridines with malonates for the first time. ► It is found that KOH was an efficient and mild catalyst for the desired ring-opening reactions. ► Good to excellent yields have been provided for a wide variety of N-tosylaziridines and malonates. ► Good to high regioselectivity are obtained in terms of most N-tosylaziridines under mild reaction conditions.