Synthesis 2015; 47(01): 129-133
DOI: 10.1055/s-0034-1379029
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

Heshmat A. Samimi*
a   Faculty of Science, Department of Chemistry, Shahrekord University, PO Box 115, Shahrekord, Iran
,
Bohari M. Yamin
b   School of Chemical Sciences and Food Technology, University Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia   Fax: +98(381)4424419   eMail: samimi-h@sci.sku.ac.ir
,
Fatemeh Saberi
a   Faculty of Science, Department of Chemistry, Shahrekord University, PO Box 115, Shahrekord, Iran
› Institutsangaben
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Publikationsverlauf

Received: 03. Juli 2014

Accepted after revision: 06. August 2014

Publikationsdatum:
17. September 2014 (online)


Abstract

A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc)2O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.

Supporting Information