71907-92-1Relevant academic research and scientific papers
Domino Wittig-Diels Alder reaction: Synthesis of carbazole lignans
Tilve, Santosh G.,Torney, Prachi S.,Patre, Rupesh E.,Kamat, Durga P.,Srinivasan, Bikshandarkoil R.,Zubkov, Fedor I.
, p. 226 - 2268 (2016)
A convenient two step protocol for the synthesis of carbazole lignans involving Domino Wittig reaction/Diels Alder reaction followed by aromatization with DDQ is described. The main step of this protocol involves interaction between 2- or 3-indolecarboxyaldehydes and cinnamyl 2-(triphenylphosphoranylidene)acetates.
A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides
Bi, Hong-Yan,Liu, Feng-Ping,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information, p. 1510 - 1516 (2018/03/05)
A tunable strategy to prepare α,β-unsaturated esters and α,β-unsaturated-γ-keto esters in good to excellent yields was developed through copper-catalyzed oxidative coupling of phosphorus ylides with alkenyl boronic acids under mild conditions. The reaction without water afforded α,β-unsaturated esters, ketones, and amides while α,β-unsaturated-γ-keto esters, 1,4-α,β-unsaturated diketones and α,β-unsaturated-γ-keto amides were obtained when using 5.0 equiv. of water. H2O18 labeling experiments showed that water played an important role in the formation of α,β-unsaturated-γ-keto esters. A plausible formation mechanism for α,β-unsaturated esters and α,β-unsaturated-γ-keto esters was proposed based on mechanistic studies. Phosphonium salts could also be used directly as coupling partners instead of phosphorus ylides. The reaction exhibited a broad substrate scope, good functional group tolerance, good regioselectivity, and diverse coupling products. (Figure presented.).
Synthesis of 1,4-enamino ketones by [3,3]-rearrangements of dialkenylhydroxylamines
Pecak, Wiktoria H.,Son, Jongwoo,Burnstine, Amy J.,Anderson, Laura L.
supporting information, p. 3440 - 3443 (2014/07/21)
The synthesis of 1,4-enamino ketones has been achieved through the [3,3]-rearrangement of dialkenylhydroxylamines generated from the addition of N-alkenylnitrones to electron-deficient allenes. The mild conditions required for this reaction, and the simultaneous installation of a fluorenyl imine N-protecting group as a consequence of the rearrangement, avoid spontaneous cyclization of the 1,4-enamino ketones to form the corresponding pyrroles and allow for the isolation and controlled divergent functionalization of these reactive intermediates. The optimization, scope, and tolerance of the new method are discussed with demonstrations of the utility of the products for the synthesis of pyrroles, 1,4-diones, and furans.
