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
Formal syntheses of (?)-isoretronecanol, (+)-laburnine, and a concise enantioselective synthesis of (+)-turneforcidine
Liang, Yu-Fu,Chung, Chuang-Chung,Huang, Meng-Wen,Uang, Biing-Jiun
, p. 397 - 406 (2019)
The synthesis of functionalized pyroglutamates 15 and 16 could be achieved by the application of recently developed diastereodivergent asymmetric Michael addition reaction of iminoglycinate 7 to ethyl γ-silyloxycrotonate with >98:2 diastereoselectivity followed by hydrolysis and lactamization. Formal syntheses of (?)-isoretronecanol and (+)-laburnine as well as a concise enantioselective synthesis of (+)-turneforcidine could be achieved from functionalized pyroglutamates 15 or 16.
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.
Stereodivergent synthesis of piperidine iminosugars 1-deoxy-D-nojirimycin and 1-deoxy-D-altronojirimycin
De Angelis, Martina,Sappino, Carla,Mandic, Emanuela,D'Alessio, Marianna,De Dominicis, Maria Grazia,Sannino, Sara,Primitivo, Ludovica,Mencarelli, Paolo,Ricelli, Alessandra,Righi, Giuliana
, (2020/12/21)
A stereodivergent approach for producing piperidine iminosugars has been developed employing a common optically active precursor. The key steps of the synthetic pathway are the double diastereoselection in the asymmetric dihydroxylation of the suitable ch
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.
Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases
Heckenbichler, Kathrin,Schweiger, Anna,Brandner, Lea Alexandra,Binter, Alexandra,Toplak, Marina,Macheroux, Peter,Gruber, Karl,Breinbauer, Rolf
supporting information, p. 7240 - 7244 (2018/06/15)
Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.
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.
NOVEL COMPOUNDS
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Page/Page column 44, (2015/12/17)
Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.
METHOD OF PREPARING AN ALKYLAMINE DERIVATIVE
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Page/Page column 5, (2012/03/10)
The present invention provides a method of preparing an alkylamine derivates which hardly generates impurities and enables mass production with high purity.
Rapid access to 6-bromo-5,7-dihydroxyphthalide 5-methyl ether by a CuBr2-mediated multi-step reaction: Concise total syntheses of hericenone J and 5′-deoxohericenone C (hericene A)
Kobayashi, Shoji,Ando, Ami,Kuroda, Hiroyuki,Ejima, Shota,Masuyama, Araki,Ryu, Ilhyong
experimental part, p. 9087 - 9092 (2011/12/01)
A practical route to 6-bromo-5,7-dihydroxyphthalide 5-methyl ether, a versatile intermediate in the synthesis of hericenones and related bioactive polyphenols, was developed. The synthesis features a combination of tandem Michael addition-Claisen condensation and CuBr2-mediated multi-step reactions. With this product in hand, total syntheses of hericenone J and 5′-deoxohericenone C (hericene A) were achieved.
