57496-47-6Relevant academic research and scientific papers
Novel CuX2-mediated cyclization of acid-base salts of (L)-cinchonidine or (D)-/(L)-α-methylbenzylamine and 2,3-allenoic acids in an aqueous medium. An efficient entry to optically active β-halobutenolides
Ma,Wu
, p. 441 - 442 (2001)
The treatment of 1:1 salts of 2,3-allenoic acid-chiral base with CuX2 (4 equiv.) in an aqueous medium, i.e. acetone-H2O (2:1), at 60-65 °C afforded β-halobutenolides with high enantiopurities in good to excellent yields.
Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: Synthesis of substituted butenolides and isocoumarins
Shi, Yili,Roth, Katrina E.,Ramgren, Stephen D.,Blum, Suzanne A.
supporting information; experimental part, p. 18022 - 18023 (2010/03/26)
(Figure Presented) A new strategy for gold and palladium dual-catalytic reactivity and turnover, called catalyzed catalysis, enhanced the synthetic usefulness of vinylgold intermediates by providing dual-catalytic carbon-carbon cross-coupling as an alternative to protodemetalation. This protocol enabled the synthesis of substituted butenolides and isocoumarins from allyl esters. Kinetic and spectroscopic experiments support a mechanism in which the Lewis acidic gold complex catalyzes both an initial rearrangement step and a subsequent Lewis basic palladium oxidative-addition step.
Ferric chloride hexahydrate-catalyzed highly regio- And stereoselective conjugate addition reaction of 2,3-allenoates with grignard reagents: An efficient synthesis of β,γ-alkenoates
Chai, Guobi,Lu, Zhan,Fu, Chunling,Ma, Shengming
supporting information; experimental part, p. 1946 - 1954 (2011/02/26)
Ferric chloride hexahydrate was shown to be an efficient catalyst for the conjugate addition of 2,3-allenoates with alkyl-, aryl-, or vinyl-Grignard reagents to synthesize polysubstituted β,γ-unsaturated alkenoates with high regio- and stereoselectivity.
Mild and efficient palladium(II)-catalyzed racemization of allenes
Horvath, Attila,Baeckvall, Jan-E.
, p. 964 - 965 (2007/10/03)
Allenes undergo racemization in the presence of catalytic amounts of Pd(OAc)2/LiBr under mild conditions; the reaction proceeds via a bromopalladation-debromopalladation sequence and tolerates various functional groups.
An Efficient Synthesis of 4-Halo-5-hydroxyfuran-2(5H)-ones via the Sequential Halolactonization and γ-Hydroxylation of 4-Aryl-2, 3-alkadienoic Acids
Ma, Shengming,Wu, Bin,Shi, Zhangjie
, p. 1429 - 1431 (2007/10/03)
4-Halo-5-hydroxyfuran-2(5H)-ones were synthesized via the efficient sequential halolactonization-hydroxylation reaction of 4-aryl-2,3-allenoic acids with I2 or CuX2 (X = Br or Cl) in moderate to good yields. The structures of the pro
