Synthesis and reactivity of trans-2-aryl-3-chloroazetidines |
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Authors: | Berten Van Driessche |
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Affiliation: | Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium |
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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. |
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Keywords: | β-Lactams Azetidines Azonio[1.1.0]bicyclobutanes |
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