1047082-71-2Relevant academic research and scientific papers
Inter-and Intramolecular Cycloaddition Reactions of Ethenetricarboxylates with Styrenes and Halostyrenes
Yamazaki, Shoko,Wang, Zhichao,Iwata, Kentaro,Katayama, Khotaro,Sugiura, Hirotaka,Mikata, Yuji,Morimoto, Tsumoru,Ogawa, Akiya
supporting information, p. 731 - 753 (2020/11/18)
Inter-and intramolecular cycloaddition reactions of ethenetricarboxylates with styrenes and α-halostyrenes have been investigated. The reactions of ethenetricarboxylates with styrenes or α-bromostyrenes in the presence of SnCl 4or SnBr 4stereoselectively gave 2,4-cis-substituted cyclobutanes. The intramolecular cycloaddition reactions of a series of styrene-functionalized ethenetricarboxylate amides, including in situ generated derivatives, showed high diversity of reaction modes depending on the structures and substituents of the substrates. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were discussed based on the DFT calculations.
P-Chiral Monophosphorus Ligands for Asymmetric Copper-Catalyzed Allylic Alkylation
Xiong, Wenrui,Xu, Guangqing,Yu, Xinhong,Tang, Wenjun
supporting information, p. 4003 - 4013 (2019/06/24)
Asymmetric copper-catalyzed allylic alkylation between allyl bromides and alkyl Grignard reagents using a P-chiral monophosphorus ligand is described. A range of terminal olefins bearing tertiary or quaternary carbon centers were formed in good branched/linear selectivities and excellent enantioselectivities at copper loadings as low as 0.5 mol %.
Transition-Metal-Free Formylation of Allylzinc Reagents Leading to α-Quaternary Aldehydes
Haraguchi, Ryosuke,Kusakabe, Akinori,Mizutani, Nakaba,Fukuzawa, Shin-Ichi
, p. 1613 - 1616 (2018/03/23)
The first example of formylation of allylzinc reagents using S-phenyl thioformate is presented. The reaction proceeded under mild conditions without any transition-metal catalyst, forming quaternary carbon centers with reactive functionalities, such as formyl and vinyl groups. Moreover, Barbier-type formylation of an allylic bromide with a sterically demanding thioformate was achieved. As a preliminary result, asymmetric formylation was conducted using a menthol-derived chiral thioformate.
Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents
Faans-Mastral, Martn,Vitale, Romina,Prez, Manuel,Feringa, Ben L.
supporting information, p. 4209 - 4212 (2015/03/14)
A copper/phosphoramidite catalyzed asymmetric allylic alkylation of Z trisubstituted allyl bromides with organolithium reagents is reported. The reaction affords all-carbon quaternary stereogenic centers in high yields and very good regio- and enantiosele
Improvements and Applications of the Transition Metal-Free Asymmetric Allylic Alkylation using Grignard Reagents and Magnesium Alanates
Grassi, David,Alexakis, Alexandre
, p. 3171 - 3186 (2015/11/03)
Two new N-heterocyclic carbene (NHC) ligands have been synthesized and employed in the transition metal-free asymmetric allylic alkylation (AAA) mediated by Grignard reagents and magnesium alanates. The employment of these ligands showed high yields and improved regio- and enantioselectivity in the formation of tertiary and quaternary stereocenters. Moreover, the low catalyst loading (up to 0.3 mol%) and high scalability (up to 10 mmol) of this improved methodology provide a convenient access to biologically active compounds and synthetically valuable intermediates.
Enantioselective synthesis of tertiary and quaternary stereogenic centers: Copper/phosphoramidite-catalyzed allylic alkylation with organolithium reagents
Fananas-Mastral, Martin,Perez, Manuel,Bos, Pieter H.,Rudolph, Alena,Harutyunyan, Syuzanna R.,Feringa, Ben L.
, p. 1922 - 1925 (2012/04/17)
An efficient and highly enantioselective copper-catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all-carbon quaternary stereogenic centers with these reactive organometallic reagents.
