Premium
Construction of 1,2,5‐Tricarbonyl Compounds using Methyl Cyanoacetate as a Glyoxylate Anion Synthon Combined with Copper(I) Iodide‐Catalyzed Aerobic Oxidation
Author(s) -
Kim Se Hee,
Kim Ko Hoon,
Kim Jae Nyoung
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100431
Subject(s) - chemistry , synthon , catalysis , iodide , glyoxylate cycle , methyl iodide , copper , aryl , organic chemistry , alkyl , medicinal chemistry , enzyme
A practical and efficient synthesis of various 1,2,5‐tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the β‐position of α,β‐unsaturated carbonyl compounds and a subsequent copper(I) iodide‐catalyzed aerobic oxidation. In addition, various α‐aryl‐ and α‐alkyl‐α‐keto esters have been synthesized using a similar approach.