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

Heshmat A. Samimi; Bohari M. Yamin; Fatemeh Saberi

doi:10.1055/s-0034-1379029

Synthesis, Table of Contents

Synthesis 2015; 47(01): 129-133
DOI: 10.1055/s-0034-1379029

paper

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

Heshmat A. Samimi*

^aFaculty of Science, Department of Chemistry, Shahrekord University, PO Box 115, Shahrekord, Iran

,

Bohari M. Yamin

^bSchool 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

^aFaculty of Science, Department of Chemistry, Shahrekord University, PO Box 115, Shahrekord, Iran

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Abstract

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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.

Key words

aziridines - regioselectivity - ring opening - reduction - nickel(II) chloride

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References

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