Oxidative Decarboxylation of α-Amino Acids with in situ Generated Dimethyl Dioxirane

Sulfur and Phosphorus Peroxides

“…The first example of oxidative decarboxylation of α-aminoacids RCH(NH 2 )COOH, in which a product other than an aldehyde or a carboxylic acid has been isolated as the major product by using Oxone, was described by Paradkar and coworkers 155 . Thus, when 1-aminocyclohexane 1-carboxylic acid was oxidized by Oxone, cyclohexanone oxime and cyclohexanone were obtained in a 3:1 ratio in 88% yield.…”

Highly efficient and stable peracid for rapid and selective oxidation of aliphatic amines to oximes

“…It can be easily transferred into various important derivatives such as amide, [1][2][3] nitrile, [4][5][6] nitro compounds, 7,8 nitrone 9 and also used for the synthesis of azoheterocycles. 10,11 Various oxidizing systems have been employed for oxidation of aliphatic amines which utilizes oxidants such as dimethyldioxirane, [12][13][14] sodium perborate 15 and sulfonic peracid, 16 oxidant-metal systems such as H 2 O 2 -nano TiO 2 , 17 H 2 O 2 -titanium superoxide, 18 H 2 O 2 -oxidoperoxidotungsten(VI) complexes, 19 H 2 O 2 -SeO 2 , 20 H 2 O 2 -with various Mo catalysts, [21][22][23] H 2 O 2 -titanium silicate (TS-1), 24,25 and TBHP-chromium silicate. 26 Though in many cases the protocol offered good oxime selectivity, the reaction requires an excess amount of oxidant with longer time for completion and often the reaction results in poor conversion.…”

A one-pot oxidative decarboxylation–Friedel-Crafts reaction of acyclic α-amino acid derivatives activated by the combination of iodobenzene diacetate/iodine and iron dust

“…The radical decarboxylation of organic carboxylic acids accompanied by simultaneous replacement by a nucleophile is an extremely useful and selective procedure in organic synthesis. 1 a-Amino acids are known to undergo oxidative decarboxylation with lead tetraacetate, 2 silver(I) acetate/peroxydisulfate, 3 trichloroisocyanuric acid, 4 N-bromosuccinimide, 5 potassium permanganate in concentrated sulfuric acid, 6 copper(II) bromidelithium tert-butoxide, 7 N-chloro-p-toluenesulfonamide sodium, 8 dimethyl dioxirane, 9 and iodosobenzene diacetate/iodine. 10 Although considerable progress has been made, decarboxylative functionalization of a-amino acids, which would open an additional route to amines, remains to be investigated (Scheme 1).…”