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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.731-740
Published online, 31st July, 2013
DOI: 10.3987/COM-13-S(S)35
Synthesis of Alkyl 3-Chloroazetidine-3-carboxylates via Regioselective Ring Transformation of Alkyl 2-(Bromomethyl)aziridine-2-carboxylates

Asta Žukauskaitė, Sven Mangelinckx, Algirdas Šačkus, and Norbert De Kimpe*

*Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium

Abstract

The synthesis of alkyl 3-chloroazetidine-3-carboxylates was developed by ring transformation of alkyl 2-(bromomethyl)aziridine-2-carboxylates utilizing ring opening with hydrochloric acid at the more sterically hindered carbon atom of the aziridine ring and subsequent base-promoted ring closure.