141377-57-3Relevant articles and documents
Synthesis of unsaturated silyl nitronates via the silylation of conjugated nitroalkenes
Khotyantseva, Elizaveta A.,Tabolin, Andrey A.,Novikov, Roman A.,Nelyubina, Yulia V.,Ioffe, Sema L.
supporting information, p. 3128 - 3131 (2018/07/13)
A new method for the synthesis of conjugated silyl nitronates from nitroalkenes is described. The procedure has wide substrate scope and is compatible with in situ generation of the substrates from 2-nitroalcohols or 2-chloro-nitroalkanes. A cascade transformation to give 3,4,5,6-tetrahydropyridine N-oxide derivatives was disclosed.
Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene
Akula, Pavan Sudheer,Hong, Bor-Cherng,Lee, Gene-Hsiang
supporting information, p. 7835 - 7839 (2019/01/04)
The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.
Preparation of Nd/Na heterogeneous catalyst from bench-stable and inexpensive Nd salt for an anti-selective catalytic asymmetric nitroaldol reaction
Nonoyama, Akihito,Hashimoto, Kazuki,Saito, Akira,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 1815 - 1819 (2016/04/05)
A Nd/Na heterobimetallic complex prepared from an amide-based chiral ligand, Nd alkoxide, and NaHMDS is a highly efficient heterogeneous catalyst for an anti-selective catalytic asymmetric nitroaldol reaction. Nd alkoxide is sensitive to moisture, expensi
Asymmetric Henry reactions catalyzed by metal complexes of chiral oxazoline based ligands
Ebru Aydin,Yuksekdanaci, Seda
, p. 14 - 22 (2013/02/23)
Chiral oxazolines have been synthesized from norephedrine and pyrrole nitrile or benzoyl chloride and applied to the catalytic asymmetric Henry reactions of p-nitro aldehydes with nitromethane to provide β-hydroxy nitroalkanols in high conversion (up to 92%). The reaction was then optimized in terms of the metal, solvent, temperature, and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and isopropanol as the solvent gave the best enantioselectivities (up to 84% ee) of the corresponding β-nitroalkanol for p-nitrobenzaldehyde.
Syn- and enantioselective henry reactions of aliphatic aldehydes and application to the synthesis of safingol
Qin, Dan-Dan,Yu, Wen,Zhou, Jie-Dan,Zhang, Yan-Cheng,Ruan, Yuan-Ping,Zhou, Zhao-Hui,Chen, Hong-Bin
supporting information, p. 16541 - 16544 (2014/01/17)
An amino alcohol copper(II) catalyst was developed for syn- and enantioselective Henry reaction of aliphatic aldehydes. Nitroethane or 2-nitroethanol and aliphatic aldehyde were sequentially added to a solution of Cu(OAc)2 H2O and li
Self-assembling neodymium/sodium heterobimetallic asymmetric catalyst confined in a carbon nanotube network
Ogawa, Takanori,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 6196 - 6201 (2013/07/19)
Confined cat works better: A self-assembling heterobimetallic catalyst, comprised of a Nd/Na/amide ligand confined in an entangled multiwalled carbon nanotube (MWNT) network, outperforms the unconfined catalyst in anti-selective catalytic asymmetric nitroaldol reactions. The confined catalyst could be used repeatedly through simple filtration, and was applied to a concise enantioselective synthesis of anacetrapib. Copyright
A Highly anti-selective asymmetric henry reaction catalyzed by a chiral copper complex: Applications to the syntheses of (+)-spisulosine and a pyrroloisoquinoline derivative
Xu, Kun,Lai, Guoyin,Zha, Zhenggen,Pan, Susu,Chen, Huanwen,Wang, Zhiyong
supporting information, p. 12357 - 12362 (2012/11/07)
A highly anti-selective asymmetric Henry reaction has been developed, affording synthetically versatile β-nitroalcohols in a predominately anti-selective manner (mostly above 15:1) and excellent ee values (mostly above 95 %). Moreover, the anti-selective Henry reaction was carried out in the presence of water for the first time with up to 99 %-ee. The catalytic mechanism was proposed based on the detection of the intermediates by extractive electrospray ionization mass spectrometry (EESI-MS). Furthermore, the anti adducts have been successfully transformed into the biochemically important (+)-spisulosine and a pyrroloisoquinoline derivative. Copyright
Promotion of Henry reactions using Cu(OTf)2 and a sterically hindered Schiff base: Access to enantioenriched β-hydroxynitroalkanes
Yao, Lin,Wei, Yu,Wang, Pingan,He, Wei,Zhang, Shengyong
, p. 9119 - 9124 (2012/10/29)
The steric and electronic properties of chiral Schiff base ligands derived from cinchona alkaloids were evaluated in asymmetric Henry reactions. Amongst these, the sterically hindered ligand 2 showed outstanding catalytic efficiency in the Cu(II) catalyze
Methylcarbonate and bicarbonate phosphonium salts as catalysts for the nitroaldol (Henry) reaction
Fabris, Massimo,Noe, Marco,Perosa, Alvise,Selva, Maurizio,Ballini, Roberto
experimental part, p. 1805 - 1811 (2012/04/17)
Phosphonium ionic liquids exchanged with bicarbonate and methylcarbonate anions (CILs) exhibit catalytic performances comparable to those of sterically hindered (non nucleophilic) organosuperbases such as DBU. At 25-50 °C, under solventless conditions, CI
Novel Schiff base ligands derived from Cinchona alkaloids for Cu(II)-catalyzed asymmetric Henry reaction
Wei, Yu,Yao, Lin,Zhang, Bangle,He, Wei,Zhang, Shengyong
experimental part, p. 8552 - 8558 (2011/11/29)
A new series of Schiff bases derived from Cinchona alkaloids were developed as chiral ligands for the copper(II)-catalyzed asymmetric Henry reaction. The optimized catalyst can promote the Henry reaction of both aromatic and aliphatic aldehydes with nitro