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Robust Synthesis of N-Sulfonylazetidine Building Blocks via Ring Contraction of α-Bromo N-Sulfonylpyrrolidinones

Nicolas Kern, Anne-Sophie Felten, Jean-Marc Weibel, Patrick Pale* and Aurélien Blanc*

*Laboratoire de Synthèse, Réactivité Organiques et Catalyse, Institut de Chimie, UMR 7177-CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France, Email: ablancunistra.fr, ppaleunistra.fr

N. Kern, A.-S. Felten, J.-M. Weibel, P. Pale, A. Blanc, Org. Lett., 2014, 16, 6104-6107.

DOI: 10.1021/ol5029496 (free Supporting Information)


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Abstract

A simple and robust one-pot nucleophilic addition-ring contraction of α-bromo N-sulfonylpyrrolidinones gives α-carbonylated N-sulfonylazetidines in the presence of potassium carbonate. Various nucleophiles, such as alcohols, phenols or anilines, have been efficiently incorporated into the azetidine derivatives. A monobromination of cheap and easily available N-sulfonyl-2-pyrrolidinone derivatives is also described.

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Key Words

Azetidines


ID: J54-Y2014