92454-52-9Relevant academic research and scientific papers
Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins
Kwon, Ohyun,Sadykhov, Gusein,Swain, Manisha,Wang, Ruoxi
supporting information, p. 17565 - 17571 (2020/09/01)
The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.
Remote Functionalization of α,β-Unsaturated Carbonyls by Multimetallic Sequential Catalysis
Romano, Ciro,Fiorito, Daniele,Mazet, Clément
supporting information, p. 16983 - 16990 (2019/10/28)
The remote functionalization of α,β-unsaturated carbonyls by an array of multimetallic sequential catalytic systems is described. The reactions are triggered by hydrometalation using [Pd-H] or [Ru-H] isomerization catalysts and driven by the formation of thermodynamically more stable 1,2-vinyl arenes. The Pd-catalyzed deconjugative isomerization was combined with a Cu-catalyzed β-borylation of the transiently generated styrenyl derivatives to deliver a range of products that would not be accessible with the use of a single catalyst. [Pd/Cu] catalytic systems were also identified for the highly enantioselective α-hydroboration and α-hydroamination of the styrenyl intermediates. Difunctionalization simultaneously at the benzylic and homobenzylic positions was achieved by combining the isomerization process with Sharpless asymmetric dihydroxylation (SAD) using [Pd/Os] or [Ru/Os] couples. Starting from a simple α,β-unsaturated ester, an isomerization/dihydroxylation/lactonization sequence gave access to a naturally occurring γ-butyrolactone in good yield, with excellent diastereo- and enantioselectivity.
Manganese(III) acetate mediated oxidative radical cyclizations. Toward vicinal all-carbon quaternary stereocenters
Logan, Angus W.J.,Parker, Jeremy S.,Hallside, Michal S.,Burton, Jonathan W.
, p. 2940 - 2943 (2012/08/28)
Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.
Oxidative and enantioselective cross-coupling of aldehydes and nitromethane catalyzed by diphenylprolinol silyl ether
Hayashi, Yujiro,Itoh, Takahiko,Ishikawa, Hayato
, p. 3920 - 3924 (2011/05/15)
Synthetically important β-substituted γ-nitro aldehydes have been synthesized with excellent enantioselectivity by the cross-coupling reaction of β-aryl substituted aldehydes or Y γ-unsaturated aldehydes and nitromethane using 2,3-dichloro-5,6-dicyanoquinone (DDQ) and diphenylprolinol silyl ether as an oxidant and catalyst, respectively (see scheme; TMS=trimethylsilyl).
Highly diastereoselective pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans
Ward, Amanda F.,Wolfe, John P.
supporting information; experimental part, p. 1268 - 1271 (2010/05/18)
Chemical Equation Presented A highly diastereoselective synthesis of substituted tetrahydrofurans bearing stereocenters at C2 and C1′ via Pd-catalyzed carboetherification reactions of acyclic internal alkenes is described. Use of an improved catalyst composed of Pd 2(dba)3/S-Phos provides products with up to >20;1 dr. The stereoselective preparation of tetrahydrofurans containing three stereocenters, including a molecule structurally related to simplakidine A, is also reported.
Heck arylations of pent-4-enoates or allylmalonate using a palladium/tetraphosphine catalyst
Lemhadri, Mhamed,Battace, Ahmed,Zair, Touriya,Doucet, Henri,Santelli, Maurice
, p. 2270 - 2281 (2007/10/03)
The Heck reaction of aryl halides with functionalised alk-1-enes should be a powerful method for the synthesis of functionalised (E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon
Controlling factors determining the regiochemistry of intramolecular alkoxymercuration
Senda, Yasuhisa,Kanto, Hiroko,Itoh, Hiroki
, p. 1143 - 1146 (2007/10/03)
The intramolecular alkoxymercuration of (E)-5-arylpent-4-en-1-ols indicated that the regioselectivity is closely related to the Hammett constants of the para-substituents on the benzene ring. Large solvent effects on the regioselectivity were also observe
