131323-45-0Relevant articles and documents
Ruthenium-Catalyzed Allylation of Primary Alcohols by Allylic Acetates: A Novel Synthesis of α,β-Unsaturated Ketones
Kondo, Teruyuki,Mukai, Takeshi,Watanabe, Yoshihisa
, p. 487 - 489 (1991)
Certain ruthenium complexes show high catalytic activity in the synthesis of α,β-unsaturated ketones from primary alcohols and allylic acetates.Here, ?-allylruthenium intermediates apparently operate as nucleophiles rather than as electrophiles.
Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium
Chen, Zhili,Hu, Fangli,Huang, Shengli,Zhao, Zhengxing,Mao, Hui,Qin, Wenling
, p. 8100 - 8111 (2019/06/17)
Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.
Decarboxylative allylation of glyoxylic acids with diallyl carbonate
Manjolinho, Filipe,Gruenberg, Matthias F.,Rodriguez, Nuria,Goossen, Lukas J.
supporting information; experimental part, p. 4680 - 4683 (2012/10/08)
A catalyst system consisting of Pd(PPh3)4 and P(pTol)3 was found to effectively promote the intermolecular decarboxylative coupling of α-oxocarboxylic acids with diallyl carbonate to give α,β-unsaturated ketones. The key advantage of the new reaction protocol is that preformation of the allyl esters is not required. The reaction is believed to proceed via phosphane-mediated decarboxylation of the α-oxocarboxylates, leading to acyl anion equivalents that are allylated within the coordination sphere of the palladium catalyst. Under the reaction conditions, the double bond then migrates into conjugation with the carbonyl group. Copyright
