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26.6.8 Product Subclass 8: α-Amino Ketones

DOI: 10.1055/sos-SD-026-00761

Suffert, J.Science of Synthesis, (200526953.

Previously published information regarding this product class can be found in HoubenWeyl, Vol. 7/2c, p 2251. Although the synthesis of α-amino ketones is important because they can be used to form biologically active β-amino alcohols and related compounds,[‌230‌,‌231‌] direct methods for their preparation are few, and none exist that start from an aliphatic ketone. However, an indirect approach depends upon the Neber rearrangement of O-tosylated ketoximes to give amino ketones.[‌223‌‌228‌] This technique was the first of its kind and it has been supplemented by several more modern alternatives. For example, nonaromatic α-amino ketones are obtained by the oxidative amination of O-silylated enols,[‌232‌] amination of α-bromo ketones,[‌233‌‌235‌] from aldehydes and iminium salts,[‌236‌] from amino acids,[‌238‌] esters,[‌239‌] amides,[‌240‌] or acyl cyanides,[‌241‌] or directly from amines.[‌242‌]