2689-60-3Relevant academic research and scientific papers
Potassium 2-oxo-3-enoates as Effective and Versatile Surrogates for α, β-Unsaturated Aldehydes in NHC-Catalyzed Asymmetric Reactions
Gao, Yaru,Ma, Yafei,Xu, Chen,Li, Lin,Yang, Tianjian,Sima, Guoqing,Fu, Zhenqian,Huang, Wei
supporting information, p. 479 - 484 (2017/12/26)
Potassium 2-oxo-3-enoates, which are readily prepared at scale and easily stored, have been found to be effective and versatile surrogates for α,β-unsaturated aldehydes in NHC-catalyzed asymmetric reactions. Promoted by chiral N-heterocyclic carbenes combined with LiCl, these easy-to-handle solid salts could release of CO2 and then undergo asymmetric reactions via homoenolate and α, β-unsaturated acyl azolium intermediate. The reactions have broad substrate scopes with high enantioselectivities. (Figure presented.).
Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
Farley, Conner M.,Zhou, You-Yun,Banka, Nishit,Uyeda, Christopher
supporting information, p. 12710 - 12714 (2018/10/09)
Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.
Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction
Liu, Xiao-Dong,Ma, Hai-Yan,Xing, Chun-Hui,Lu, Long
supporting information, p. 1780 - 1783 (2017/07/27)
NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.
Crossed intramolecular rauhut-currier-type reactions via dienamine activation
Marques-Lopez, Eugenia,Herrera, Raquel P.,Marks, Timo,Jacobs, Wiebke C.,Koenning, Daniel,De Figueiredo, Renata M.,Christmann, Mathias
supporting information; experimental part, p. 4116 - 4119 (2009/12/06)
The intramolecular Rauhut-Currier reaction creates a carbon-carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we Investigate a novel strategy that involves the formation of electron rich dienamines as key Intermediates. Our methodology provides an efficient entry to the iridoid framework.
New access to trisubstitutea 3-pyrrolines under phosphine catalysis
Schuler, Marie,Duvvuru, Deepti,Retailleau, Pascal,Betzer, Jean-Francois,Marinetti, Angela
supporting information; scheme or table, p. 4406 - 4409 (2009/12/26)
Conjugated dienes, properly activated by electron-withdrawing groups on both ends, are shown to be suitable substrates for phosphinepromoted organocatalytic processes. Their reactions with imines, under phosphine catalysis, afford a new and efficient synthetic approach to functionalized 3-pyrrolines.
Synthesis and characterization of transition metal (Hg(II), Ag(I) and Cd(II)) complexes of some new: Phosphorus ylides
Sabounchei, S. Javad,Jodaian, Vida,Nemattalab, Hassan
experimental part, p. 9 - 13 (2010/08/19)
Reaction of two new phosphorus ylides Ph3PCHCOC 10H7 (Y1) and Ph3PCHCOC 4H3S(Y2) with mercury(II) halides and a previously reported ylide (P-tolyl)3PCHCOOCH
Chemically Induced Anion Radical Cycloadditions: Intramolecular Cyclobutanation of Bis(enones) via Homogeneous Electron Transfer
Yang, Jingkui,Felton, Greg A. N.,Bauld, Nathan L.,Krische, Michael J.
, p. 1634 - 1635 (2007/10/03)
The first examples of anion radical cycloaddition induced by homogeneous electron transfer from chemical agents are described. Specifically, upon exposure to chrysene anion radical, bis(enone) substrates are found to engage in stereoselective intramolecular [2 + 2] cycloaddition. These studies, along with the corresponding electrochemically initiated reactions, provide insight into this fundamentally new pattern of reactivity and support the feasibility of expanding this novel reaction type. Copyright
