Facile regiocontrolled three-step synthesis of poly-substituted furans, pyrroles, and thiophenes: Consecutive michael addition of methyl cyanoacetate to α,β-enone, CuI-mediated aerobic oxidation, and acid-catalyzed paal-knorr synthesis
An efficient synthesis of poly-substituted furans, pyrroles, and thiophenes was carried out in a regiocontrolled manner via a three-step process; (i) conjugate addition of methyl cyanoacetate derivatives to α,β-enones, (ii) CuI-mediated aerobic oxidation,
Kim, Se Hee,Lim, Jin Woo,Lim, Cheol Hee,Kim, Jae Nyoung
scheme or table
p. 620 - 624
(2012/05/05)
Construction of 1,2,5-tricarbonyl compounds using methyl cyanoacetate as a glyoxylate anion synthon combined with copper(I) iodide-catalyzed aerobic oxidation
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. Copyright
Kim, Se Hee,Kim, Ko Hoon,Kim, Jae Nyoung
supporting information; experimental part
p. 3335 - 3339
(2012/01/19)
Etude de la reaction de Michael en presence de divers agents complexants des cations alcalins en milieu aprotique ou dans les conditions de transfert de phase
Michael addition of methyl cyanoacetate to benzylideneacetophenone 5a or benzylideneacetone 5b, in THF, under LiOt-Bu or KF catalysis takes place only in the presence of complexing agents for the cation.With LiO.t.Bu, HMPA, diHMPA, NIPA or 12-crown-4 show