Wenker-Synthesis

This reaction sequence allows the preparation of aziridines from 1,2-amino alcohols.

---

Mechanism of the Wenker Synthesis

After preparation of sulphonate salt, a second deprotonation step effects the ring closure:

Recent Literature

An Improved and Mild Wenker Synthesis of Aziridines
X. Li, N. Chen, J. Xu, Synthesis, 2010, 3315-3318.

Synthesis of N-H vinylaziridines: a comparative study
B. Olofsson, R. Wijtmans, P. Somfai, Tetrahedron, 2002, 58, 5979-5982.

Short and Efficient Synthesis of Optically Active N-Tosyl Aziridines from 2-Amino Alcohols
L. W. Bieber, M. C. F. de Araujo, Molecules, 2002, 7, 902.

Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes
N. Hsueh, G. J. Clarkson, M. Shipman, Org. Lett., 2015, 17, 3632-3635.