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N-Arylazetidines: Preparation through Anionic Ring Closure

Pierre Quinodoz, Bruno Drouillat, Karen Wright, Jérôme Marrot and François Couty*

*Institut Lavoisier de Versailles, UMR 8180. Université de Versailles St-Quentin-en-Yvelines, Université Paris Saclay, 45, Avenue des Etats-Unis, Versailles 78035 Cedex, France, Email: coutychimie.uvsq.fr

P. Quinodoz, B. Drouillat, K. Wright, J. Marrot, F. Couty, J. Org. Chem., 2016, 81, 2899-2910.

DOI: 10.1021/acs.joc.6b00169 (free Supporting Information)


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Abstract

Diversely substituted N-aryl-2-cyanoazetidines can be prepared in high yields from β-amino alcohols in enantiomerically pure form through a three-step sequence involving copper-catalyzed N-arylation, N-cyanomethylation of the secondary aniline, and one-pot mesylation followed by ring closure induced by a base. This method gives access to azetidines with a predictable and adjustable substitution pattern and also with predictable diastereoselectivity.


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Key Words

azeditines


ID: J42-Y2016