2520-60-7Relevant academic research and scientific papers
Convenient Radical α-Monoallylations of Carbonyl Compounds
Watanabe, Yoshihiko,Yoneda, Tetsuo,Okumura, Tatsuya,Ueno, Yoshio,Toru, Takeshi
, p. 3030 - 3033 (1993)
Free radical allylations of α-seleno carbonyl compounds with tributyl-substituted 2,4-pentadienyltin, 2-methyl-2-propenyltin, 2-butenyltin, and 3-methyl-2-butenyltin, are described. Such successful C-C bond formations, in particular with the 2-butenyltin and the 3-methyl-2-butenyltin, are owing to the high reactivity of the α-carbon radical, generated from α-seleno carbonyl compounds, toward allylic tin compounds.
Direct palladium-catalyzed allylic alkylations of alcohols with enamines: Synthesis of homoallyl ketones
Bouhalleb, Ghalia,Mhasni, Olfa,Poli, Giovanni,Rezgui, Farhat
, p. 2525 - 2529 (2017)
An efficient, direct nucleophilic allylic substitution of α-, β- and γ-substituted alcohols with enamines, using the Pd(OAc)2/PPh3 catalyst system and ZnBr2 as a promoter in CH2Cl2 at reflux, is reported. The reaction course was dependent on the steric hindrance at the α- or γ-positions with respect to the functionalized α-carbon, selectively affording in moderate to good yields, α- or γ-homoallyl ketones, the so-called “linear” and “branched” products, respectively.
Synthesis of Prenylated Indoles
Wenkert, Ernest,Angell, E. Charles,Ferreira, Vitor F.,Michelotti, Enrique L.,Piettre, Serge R.,et al.
, p. 2343 - 2351 (2007/10/02)
Interaction of magnesium indolates and allyl oxides in the presence of bis(triphenylphosphine)nickel dichloride results in indole β-allylation, except in cases involving highly substituted indoles and allyl alcohols.This method permits the β-prenylation of indole and α-prenylation of ketones (by way of their magnesium enaminates).Base-induced interaction of ethynyldimethylcarbinyl chloride and indole under a variety of conditions yields β-(β,β-dimethylvinyl)quinoline as well as variously dehydroprenylated indoles. α-Lithiation of N-(benzenesulfonyl)indole followed by treatmentwith prenyl bromide or β,β-dimethylacrylyl chloride produces α-prenyl- or α-oxoprenylidole derivatives, the sodium amalgam reduction of the former of which yields α-prenylidole.Interaction of β-cuprated N-(benzenesulfonyl)indole with the same halides followed by reduction affords β-prenylindole and β-oxoprenylindole, the latter also being the product of the reaction of magnesium indolate and the acid chloride.Lithium aluminum hydride reduction of 1-(benzenesulfonyl)-3-oxoprenylindole affords an alcohol, whose base hydrolysis produces β-dehydroprenylindole, a compound whose dimerization has led previously to naturally occuring yuehchukene.
