In 2022,Ong, Mike; Arnold, Marlene; Walz, Alexander W.; Wahl, Johannes M. published an article in Organic Letters. The title of the article was 《Stereospecific Nitrogen Insertion Using Amino Diphenylphosphinates: An Aza-Baeyer-Villiger Rearrangement》.Product Details of 36016-38-3 The author mentioned the following in the article:
Amino diphenylphosphinates, which are com. available or easily prepared from hydroxylamine, underwent ring expansion of cyclobutanones toward γ-lactams under mild conditions. A reaction pathway profoundly different from the common Beckmann reaction was achieved through the ambivalent character of the aminating agent. Thus, rearrangement occurred from a Criegee-like intermediate prior to the formation of the oxime species, which was corroborated by mechanistic experiments Based on this observation, the migrating aptitude of the adjacent groups was analyzed and found to be in line with the parent Baeyer-Villiger reaction rendering a regioselective (up to >99:1 rr), stereospecific (>99% enantiospecificity) and chemoselective (>99%) insertion process possible. The method thus qualifies for late-stage skeletal editing as showcased by the synthesis of Rolipram and its N-alkylated analogs. The experimental process involved the reaction of N-tert-Butoxycarbonylhydroxylamine(cas: 36016-38-3Product Details of 36016-38-3)
N-tert-Butoxycarbonylhydroxylamine(cas: 36016-38-3) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Product Details of 36016-38-3
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