5267-68-5Relevant articles and documents
Direct enantioselective C(sp3)-H acylation for the synthesis of α-amino ketones
Shu, Xiaomin,Huan, Leitao,Huang, Qian,Huo, Haohua
, p. 19058 - 19064 (2020)
A direct enantioselective acylation of α-amino C(sp3)-H bonds with carboxylic acids has been achieved via the merger of transition metal and photoredox catalysis. This straightforward protocol enables cross-coupling of a wide range of carboxylic acids, one class of feedstock chemicals, with readily available N-alkyl benzamides to produce highly valuable α-amino ketones in high enantioselectivities under mild conditions. The synthetic utility of this method is further demonstrated by gram scale synthesis and application to late-stage functionalization. This method provides an unprecedented solution to address the challenging stereocontrol in metallaphotoredox catalysis and C(sp3)-H functionalization. Mechanistic studies suggest the α-C(sp3)-H bond of the benzamide coupling partner is cleavage by photocatalytically generated bromine radicals to form α-amino alkyl radicals, which subsequently engages in nickel-catalyzed asymmetric acylation.
Rapid synthesis of oxazoles under microwave conditions
Brain, Christopher T.,Paul, Jane M.
, p. 1642 - 1644 (2007/10/03)
A new and efficient variation of the Robinson-Gabriel oxazole synthesis is described. Oxazoles were prepared by cyclodehydration of 2-acylamino carbonyl compounds with Burgess reagent under monomode microwave irradiation.
