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Synthesis of N-H vinylaziridines: a comparative study

Berit Olofsson, Roel Wijtmans and Peter Somfai*

*Organic Chemistry, Department of Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden, Email: peter.somfaichem.lu.se

B. Olofsson, R. Wijtmans, P. Somfai, Tetrahedron, 2002, 58, 5979-5982.

DOI: 10.1016/S0040-4020(02)00610-5


Abstract

Vinylaziridines are useful and versatile synthetic intermediates, as the relief of ring-strain provides a driving force for efficient ring-opening or ring-expansion reactions. Furthermore, the vinyl group can be derivatized into interesting functionalities. The ring-closure of vicinal amino alcohols constitutes a straightforward route to aziridines. Several methods exist for this transformation, although many cannot be applied to vinylaziridines due to their acid lability. This comparative study describes the most effective sequences for the formation of N-H vinylaziridines.

Via Mitsunobu cyclization:

By activation of the hydroxy group: 

By activation of the amino group:

see article for more reactions

The tritylated amino alcohol can also by converted to the aziridine via mesylate or cyclic sulfamidate (see article).



Key Words

Amino Alcohols, Aziridines, Vinylaziridines, Mitsunobu Reaction, Wenker Synthesis


ID: J72-Y2002-060.