10080-68-9Relevant articles and documents
Ru(II)-Pheox-catalyzed asymmetric intramolecular cyclopropanation of electron-deficient olefins
Nakagawa, Yoko,Chanthamath, Soda,Shibatomi, Kazutaka,Iwasa, Seiji
, p. 2792 - 2795 (2015)
The first highly enantioselective intramolecular cyclopropanation of electron-deficient olefins, in the presence of Ru(II) - Pheox catalyst, is reported. The corresponding cyclopropane-fused γ-lactones were obtained in high yields (up to 99%) with excelle
Catalytic asymmetric carbonyl-ene reactions with alkynylogous and vinylogous glyoxylates: Application to controlled synthesis of chiral isocarbacyclin analogues
Mikami, Koichi,Yoshida, Akihiro,Matsumoto, Youichi
, p. 8515 - 8518 (1996)
The asymmetric carbonyl-ene reaction with alkynylogous and vinylogous glyoxylates (1, 2) catalyzed by a binaphthol-derived chiral titanium complex is described. The catalytic asymmetric ene reaction with aldehyde (1) can be applied to the double asymmetric synthesis of isocarbacyclin analogues bearing a 2-allenyl side chain.
Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives
Bitai, Jacqueline,Slawin, Alexandra M.Z.,Cordes, David B.,Smith, Andrew D.
supporting information, (2020/07/27)
The scope and limitations of a tandem N-allylation/[2,3]-rearrangement protocol are investigated through the incorporation of a variety of functional groups within an allylic phosphate precursor. This method uses readily accessible N,N-dimethylglycine aryl esters and functionalized allylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequent enantioselective [2,3]-sigmatropic rearrangement, promoted by the chiral isothiourea tetramisole, generates α-amino acid derivatives with two contiguous stereocenters. The incorporation of electron-withdrawing ester and amide groups gave the best results, furnishing the desired products in moderate to good yields (29-70percent), with low diastereocontrol (typically 60:40 dr) but high enantioselectivity (up to 90:10 er). These results indicate that substrate-catalyst interactions in the proposed transition state are sensitive to the substitution pattern of the substrates.
Syn-effect' in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones
Jiménez, Jacqueline,Ramírez, Juáncarlos,Huelgas, Gabriela,Meléndrez, Ruth,Cabrera-Vivas, Blanca M.,Sansinenea, Estibaliz,Ortiz, Aurelio
, p. 4590 - 4597 (2015/06/08)
Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O.