66150-50-3Relevant academic research and scientific papers
Bismuth- and Iron-Catalyzed Three-Component Synthesis of α-Amino Acid Derivatives: A Simple and Convenient Route to α-Arylglycines
Halli, Juliette,Schneider, Angelika E.,Beisel, Tamara,Kramer, Philipp,Shemet, Andrej,Manolikakes, Georg
, p. 849 - 879 (2017/02/15)
Efficient bismuth- and iron-catalyzed three-component syntheses of α-arylglycines have been developed. These methods provide a general, atom-economic route to various N-protected α-arylglycines starting from readily available amides (or carbamates), glyoxalates, and (hetero)arenes with water as the only by-product. Scope and limitations of bismuth- and iron-catalyzed reactions are discussed and compared. In addition, mechanistic investigations as well as initial forays into stereoselective three-component reactions are presented.
Simple and efficient synthesis of racemic substituted mandelic acid esters from nonactivated arenes and ethyl glyoxylate
Kwiatkowski, Jacek,Majer, Jakub,Kwiatkowski, Piotr,Jurczak, Janusz
experimental part, p. 3237 - 3244 (2009/05/26)
Direct synthesis of racemic aromatic α-hydroxyacetic acid esters via Friedel-Crafts reaction of nonactivated, simple arenes with ethyl glyoxylate promoted by SnCl4 or AlCl3 is described. The use of SnCl4 opens a fast access to various alkyl- and aryl-substituted mandelic acids esters at room temperature within two hours in good yield (>80%) and with high regioselectivity. The procedure was successfully employed also for the alkylation of compounds with condensed aromatic rings. Alternative hydroxyalkylations with AlCl3 require longer reaction time and higher temperature to get a good yield.
