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A versatile and one-pot strategy to synthesize α-amino ketones from benzylic secondary alcohols using N -bromosuccinimide
Date Issued
06-02-2015
Author(s)
Guha, Somraj
Rajeshkumar, Venkatachalam
Kotha, Surya Srinivas
Indian Institute of Technology, Madras
Abstract
A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important α-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new 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. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step.
Volume
17