Synlett 2014; 25(2): 201-204
DOI: 10.1055/s-0033-1340108
letter
© Georg Thieme Verlag Stuttgart · New York

Brønsted Acid Catalyzed Amination of 1,3-Dicarbonyl Compounds by Iminoiodanes

Ciputra Tejo
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6567911961   Email: waihong@ntu.edu.sg
,
Hui Quan Yeo
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6567911961   Email: waihong@ntu.edu.sg
,
Philip Wai Hong Chan*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore   Fax: +6567911961   Email: waihong@ntu.edu.sg
› Author Affiliations
Further Information

Publication History

Received: 24 September 2013

Accepted after revision: 08 October 2013

Publication Date:
19 November 2013 (online)


Abstract

A synthetic method to aminate 1,3-dicarbonyl compounds with PhI=NTs using Brønsted acid catalysis is described herein. The method was shown to be applicable to β-keto esters and phosphonates as well as 1,3-diones, providing the corresponding α,α-acyl amino acid derivatives in moderate to excellent yields.

Supporting Information

 
  • References and Notes


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  • 7 General Procedure To a degassed mixture of PhI=NTs (0.6 mmol, 224 mg) and powdered 4 Å MS (240 mg) was added CH2Cl2 (1 mL). The reaction was cooled to 0 °C, and a solution of TFA (0.05 mmol, 3.83 μL) in CH2Cl2 (1 mL) was added. The 1,3-dicarbonyl compound was added, and the reaction was monitored by TLC analysis. Upon completion, the reaction mixture was filtered, washed with EtOAc (40 mL), concentrated under reduced pressure, and purified by flash chromatography [n-hexane–EtOAc (4:1) as eluent] to furnish the title compound.
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