Berten Van Driessche, Willem Van Brabandt, M. D’hooghe
Jul 17, 2006
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron
Abstract
Abstract Several trans-2-aryl-3-chloroazetidines were synthesized in a stereoselective way by reduction of the corresponding β-lactams, which were formed by a Staudinger reaction using different benzaldimines and chloroketene. The resulting chloroazetidines proved to be excellent building blocks for the synthesis of different 3-substituted azetidines through nucleophilic substitution of the chlorine by different carbon, nitrogen, sulfur and oxygen nucleophiles in good to high yields. Since these substitution reactions took place with retention of stereochemistry, the intermediacy of bicyclic azonio[1.1.0]bicyclobutanes is proposed.