41303-44-0Relevant articles and documents
Ligand-Controlled Regiodivergence in Nickel-Catalyzed Hydroarylation and Hydroalkenylation of Alkenyl Carboxylic Acids**
Deng, Ruohan,Engle, Keary M.,Fu, Yue,Gao, Yang,Li, Zi-Qi,Liu, Peng,Tran, Van T.
supporting information, p. 23306 - 23312 (2020/10/19)
A nickel-catalyzed regiodivergent hydroarylation and hydroalkenylation of unactivated alkenyl carboxylic acids is reported, whereby the ligand environment around the metal center dictates the regiochemical outcome. Markovnikov hydrofunctionalization products are obtained under mild ligand-free conditions, with up to 99 % yield and >20:1 selectivity. Alternatively, anti-Markovnikov products can be accessed with a novel 4,4-disubstituted Pyrox ligand in excellent yield and >20:1 selectivity. Both electronic and steric effects on the ligand contribute to the high yield and selectivity. Mechanistic studies suggest a change in the turnover-limiting and selectivity-determining step induced by the optimal ligand. DFT calculations reveal that in the anti-Markovnikov pathway, repulsion between the ligand and the alkyl group is minimized (by virtue of it being 1° versus 2°) in the rate- and regioselectivity-determining transmetalation transition state.
Synthesis of 1-tetralone derivatives using a Stille cross coupling/friedel crafts acylation sequence
Vercouillie, Johnny,Abarbri, Mohamed,Parrain, Jean-Luc,Duchene, Alain,Thibonnet, Jerome
, p. 3751 - 3762 (2007/10/03)
An efficient method of synthesis of 1-tetralones has been achieved featuring a Stille cross-coupling reaction as the key step.
Total synthesis of homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine
Tsuda, Yoshisuke,Ohshima, Takeshi,Hosoi, Shinzo,Kaneuchi, Satomi,Kiuchi, Fumiyuki,Toda, Jun,Sano, Takehiro
, p. 500 - 508 (2007/10/03)
Total syntheses of two homoerythrinan alkaloids, schelhammericine and 3-epischelhammericine, are described. Photocycloaddition of a dioxopyrrolobenzazepine to 1-methoxy-3-trimethylsilyloxybutadiene afforded, in a regio- and stereo-specific manner, the cyc
