Efficient Ring Opening of Aziridines with Carboxylic Acids

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 steps.

Keywords:

• Amino alcohols
• amino esters
• unactivated aziridines

Acknowledgment

V. K. S. thanks the Department of Science and Technology, Government of India, for a research grant. S. G. thanks the Council of Scientific and Industrial Research, New Delhi, for a senior research fellowship.