83984-74-1Relevant academic research and scientific papers
Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane
Chen, Xue,Jin, Hongwei,Liu, Yunkui,Wang, Zhen,Zhou, Bingwei,Zhou, Jinyong
supporting information, p. 8021 - 8024 (2021/10/04)
Herein we describe a nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane. A range ofZ-silyl enol ethers are obtained as major isomers due to the process of nickel triggered alkene isomerization. Notably, some specific
Highly Enantioselective Construction of Dihydrooxazines via Pd-Catalyzed Asymmetric Carboetherification
Li, Na,Sun, Baozhen,Liu, Shuang,Zhao, Jinbo,Zhang, Qian
supporting information, p. 190 - 193 (2020/01/02)
A straightforward synthesis of highly enantioenriched 5,6-dihydro-4H-1,2-oxazines is realized by Pd-catalyzed asymmetric carboetherification of γ,δ-alkenyl oximes with (hetero)aryl and alkenyl halides in the presence of a commercially available bisphosphine ligand. The enantioenriched products can be facilely converted to functionalized alcohols with high fidelity of chiral transfer.
Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Zhang, Mengru,Liu, Shuang,Li, Hexin,Guo, Yajing,Li, Na,Guan, Meihui,Mehfooz, Haroon,Zhao, Jinbo,Zhang, Qian
supporting information, p. 12620 - 12627 (2019/09/16)
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.
Cobalt-Catalyzed Stereoselective Synthesis of 2,5- trans-THF Nitrile Derivatives as a Platform for Diversification: Development and Mechanistic Studies
Ali, Sajjad,Milanezi, Henrique,Alves, Tania M. F.,Tormena, Cláudio Francisco,Ferreira, Marco A. B.
, p. 7694 - 7713 (2018/06/18)
A straightforward protocol integrating a sustainable approach for the synthesis of new 2,5-trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substit
Organocatalytic synthesis of polysubstituted tetrahydrofurans from alkenes
Theodorou, Alexis,Kokotos, Christoforos G.
supporting information, p. 670 - 674 (2017/08/18)
A novel, organocatalytic and environmentally friendly protocol for the synthesis of polysubstituted tetrahydrofurans from trivial starting materials has been described. By employing 2,2,2-trifluoroacetophenone-mediated oxidation, which utilizes H2O2 as a green oxidant, we introduce a sustainable procedure that embraces the principles of green chemistry for the production of substituted tetrahydrofurans in high to excellent yields and tolerates a wide range of substitution patterns.
Investigating the arenyl-diene double [3 + 2] photocycloaddition reaction
Penkett, Clive S.,Woolford, Jason A.,Read, Timothy W.,Kahan, Rachel J.
, p. 1295 - 1304 (2011/04/26)
The double [3 + 2] photocycloaddition reaction involving arenyl-dienes has been used to assemble seven separate [5.5.5.5] fenestrane structures that include ether and aza variants. The primary photolysis step was a meta photocycloaddition reaction, while
Polar and steric substituent effects in 5-exo-trig cyclizations of 1-aryl-4-penten-1-oxyl radicals
Hartung, Jens,Hiller, Margit,Schmidt, Philipp
, p. 1425 - 1436 (2007/10/03)
A series of 1-aryl-substituted 4-penten-1-oxyl radicals 2 were generated from parent N-alkoxypyridinethiones 6. The intermediates 2 undergo 5-exo-trig cyclizations which are sensitive to polar and steric substituent effects. Thus, para groups in the aroma
Lithium Dialkylamide Induced 1,4-Elimination of Methyl o-Methylbenzyl Ethers: Formation and Reactions of o-Xylylenes
Tuschka, Theodore,Naito, Katsuyuki,Rickborn, Bruce
, p. 70 - 76 (2007/10/02)
Lithium dialkylamide induced 1,4-elimination is shown to be a general reaction of methyl o-methylbenzyl ethers, giving o-xylylenes as reactive intermediates.The fate of the intermediates depends on a variety of factors including the base used, the dienophile employed as solvent, or the presence of a suitable located double bond in the substrate.With lithium diisopropylamide (LDA), a significant reaction forms the amine derived from 1,4-addition to o-xylylene.The use of lithium tetramethylpiperidide (LTMP) avoids this addition and allows the study of in situ generated o-xylylene in intermolecular Diels-Alder reactions with simple olefins, where dimerization/polymerization is the major competing pathway.Yields of Diels-Alder adducts range from negligible (cyclohexene) to high (norbornene), with 1-hexene, isoprene, and cyclopentene giving intermediate values.Intramolecular Diels-Alder reactions to form six- and five-membered rings proceed well but are not observed for lower homologue.Second-order rate constants have been obtained for the elimination reaction of some of the substrate ethers, and the effects of structure and temperature on yields of cycloadduct are examined.LTMP is about twice as reactive as LDA in these 1,4-eliminations.
