141811-82-7Relevant articles and documents
Synthesis and reactivity of trans-2-aryl-3-chloroazetidines
Van Driessche, Berten,Van Brabandt, Willem,D'hooghe, Matthias,Dejaegher, Yves,De Kimpe, Norbert
, p. 6882 - 6892 (2006)
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.