A One-Pot Synthesis of trans-N-Alkylaziridine-2-carboxylates from Amino Alcohol Esters

Abstract

A series of new trans-N-alkylaziridine-2-carboxylates 3 was conveniently synthesized in a one-pot reaction by treatment of 1,2-amino alcohol mono and diesters 1 with methanesulfonyl chloride in the presence of (iPr)₂NEt. The products were obtained in good to excellent yields with high trans-selectivity.

Keywords:

• Amino alcohols mono and diesters
• methanesulfonyl chloride
• trans-N-alkylaziridine-2-carboxylates

ACKNOWLEDGMENTS

We thank Prof. R. Mercier (Université Savoie) for providing the microanalysis and Dr. M. A. Sanhoury, Member of the Royal Society of Chemistry (MRSC) of the Department of Chemistry, Faculty of Sciences of Tunis, for helpful discussions.

Notes

^a Yields refer to isolated chromatographically pure compounds.

^b This product was previously prepared from ethyl α-bromocinammate.^{[ 18 ]}