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A Versatile and One-Pot Strategy to Synthesize α-Amino Ketones from Benzylic Secondary Alcohols Using N-Bromosuccinimide

Somraj Guha, Venkatachalam Rajeshkumar, Surya Srinivas Kotha and Govindasamy Sekar*

*Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600036, India, Email: gsekariitm.ac.in

S. Guha, V. Rajeshkumar, S. S. Kotha, G. Sekar, Org. Lett., 2015, 17, 406-409.

DOI: 10.1021/ol503683q (free Supporting Information)



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Abstract

The use of N-bromosuccinimide enables a metal-free one-pot strategy for the synthesis of pharmaceutically important α-amino ketones from readily available benzylic secondary alcohols and amines. This reaction proceeds via three consecutive steps involving oxidation of alcohols, α-bromination of ketones, and nucleophilic substitution of α-bromo ketones to give α-amino ketones.


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Key Words

α-amination, NBS


ID: J54-Y2015