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40.1.1.4.2.3 Method 3: Neber Rearrangement

DOI: 10.1055/sos-SD-040-00241

Purchase, R.; Sainsbury, M.Science of Synthesis, (200940394.

α-Amino ketones 151 can be synthesized when O-tosyl ketoximes 149 are treated with a base, such as pyridine or the ethoxide ion.[‌175‌] This reaction is called the Neber rearrangement {see Science of Synthesis, Vol. 26 [Ketones (Section 26.6.8.1.126.6.8.1.1)] and Section 40.1.5.1.2.5} and is normally carried out when the substituent R1 is aryl; nevertheless, R1 can also be hydrogen or alkyl, but R2 may only be alkyl or aryl. Beckmann (to an amide) or abnormal Beckmann (elimination to form a nitrile) rearrangements may complicate the outcome of the Neber reaction, although these competing reactions normally require acidic conditions. The Neber rearrangement operates through the initial formation of an azirine 150 that is subsequently hydrolyzed to the amine (Scheme 44).[‌176‌,‌177‌]

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