503624-63-3Relevant academic research and scientific papers
Palladium-catalyzed enantioselective ring opening of oxabicyclic alkenes with organozinc halides
Li, Ming,Yan, Xiao-Xia,Hong, Wei,Zhu, Xia-Zhen,Cao, Bo-Xun,Sun, Jie,Hou, Xue-Long
, p. 2833 - 2835 (2004)
Palladium-catalyzed asymmetric ring opening of oxabenzonorbornadienes with readily available organozinc halides under mild conditions in the presence of (S)-Pri-PHOX produces the corresponding 1,2-dihydronaphth-1-ols in good yield and high enan
Transition metal complexes of fesulphos ligands in enantioselective catalytic transformations
Arrayas, Ramon Gomez,Mancheno, Olga Garcia,Cabrera, Silvia,Carretero, Juan Carlos
, p. 1259 - 1265 (2005)
Metal complexes of 1-phosphino-2-sulfenylferrocene (fesulphos ligands) act as highly efficient catalysts in Pd-catalyzed desymmetrization of meso heterobicyclic alkenes and in Cu-catalyzed formal aza Diels-Alder reaction of Danishefsky diene to N-sulfonyl
Iridium/Copper Co-catalyzed Anti-Stereoselective Ring Opening of Oxabenzonorbornadienes with Grignard Reagents
Cheng, Guo,Yang, Wen,Li, Yue,Yang, Dingqiao
, p. 7817 - 7823 (2016)
Cooperative catalysis has been widely considered as one of the most powerful strategies to improve synthetic efficiency. A new iridium/copper cocatalyst was developed for the ring-opening reaction of oxabenzonorbornadienes with a wide variety of Grignard reagents, which afforded the corresponding anti-2-substituted 1,2-dihydronaphthalen-1-ols in high yields (up to 99% yield) under mild conditions. The effects of catalyst loading, Lewis acid, Grignard reagent loading, and reaction temperature on the yield were investigated. To the best of our knowledge, it represents the first example of ring-opening reactions of oxabicyclic alkenes with Grignard reagent nucleophiles in a trans-stereoselective manner.
Multinuclear Pd/Zn complex-catalyzed asymmetric alkylative ring-opening reaction of oxabicyclic alkenes
Endo, Kohei,Tanaka, Keisuke,Ogawa, Mika,Shibata, Takanori
, p. 868 - 871 (2011)
A multinuclear palladium catalyst can be used to realize the efficient catalytic asymmetric alkylative ring-opening reaction of oxabicyclic alkenes using dimethylzinc. The use of (R)-BINOL-PHOS bearing bisphosphine and diol moieties is essential for achieving excellent catalytic performance; the corresponding monophosphine and hydroxy-protected derivatives showed lower catalytic activities and/or enantioselectivities. The generation of Pd/Zn-multinuclear complexes is a key feature of the present catalysis.(Figure Presented)
Nickel-catalyzed: Syn -stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents
Deng, Yingying,Yang, Wen,Yao, Yongqi,Yang, Xin,Zuo, Xiongjun,Yang, Dingqiao
, p. 703 - 711 (2019/01/24)
A new nickel-catalyzed syn-stereocontrolled ring-opening of oxa- and azabicyclic alkenes with dialkylzinc reagents was developed, which afforded the corresponding cis-2-alkyl-1,2-dihydronaphthalen-1-ols and 1,2-alkyl amide derivatives in moderate to excellent yields (up to 99% yield) under mild conditions. In this work, we successfully avoided obtaining hydride addition byproducts arising from β-hydride elimination on an ethyl nickel species. Furthermore, a plausible mechanism for the ring-opening reaction was also proposed.
Synthesis method of chiral compound of hydrogenated naphthalene structure unit
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Paragraph 0027; 0031; 0032, (2018/06/26)
The invention discloses a synthesis method of a chiral compound of a hydrogenated naphthalene structure unit. In a methylbenzene/water solvent system, under the existence of catalysts of palladium acetate and R-(+)-1,1'-dinaphthalene-2,2'-diphenylphosphane, potassium trifluoroborate derivatives and oxa-benzo norbornene react at the room temperature to obtain the chiral compound of the hydrogenatednaphthalene structure unit through synthesis. The method provided by the invention has the advantages that the raw materials are cheap and can be easily obtained; the reaction conditions are mild; the post treatment is simple; the obtained target product yield and ee value are high.
Phosphoramidite Ligands Based on Simple 1,2-Diols: Synthesis, Use in Copper-Catalyzed Asymmetric Additions, and Achirotopic Stereogenic Phosphorus Centres
Mistry, Nisha,Fletcher, Stephen P.
supporting information, p. 2489 - 2496 (2016/08/16)
Phosphoramidite ligands are widely used in catalysis and normally constructed from large C2-symmetrical diols such as BINOL or TADDOL. We report here on new ligands based on a set of simple diols that had been previously overlooked. Ligands based on (S,S)-trans-cyclohexanediol and (R,R)-(+)-1,2-diphenyl-1,2-ethanediol, in combination with both chiral and achiral amines, were tested in 3 different copper-catalyzed asymmetric reactions and up to 89% ee was observed. A different ligand gave the best results in each reaction examined. Using meso-cis-cyclohexanediol and meso-cis-diphenyl-1,2-ethanediol with a chiral non-racemic amine gave diastereomeric ligands bearing achirotopic stereogenic phosphorus atoms which were characterized with the assistance of X-ray crystallography and variable temperature NMR studies. This work provides a new set of ligands that may be useful in some asymmetric reactions when phosphoramidites based on BINOL and TADDOL are ineffective. We also identify a novel stereochemical feature of phosphoramidites that may be useful in asymmetric catalysis and ligand design. (Figure presented.).
Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents
Yang, Dingqiao,Liang, Ni
, p. 2080 - 2086 (2014/03/21)
A new platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with various Grignard reagents was reported, which afforded the corresponding anti-2-substituted-1,2-dihydronaphthalen-1-ol products with moderate to good yields in the presence of a catalytic amount of Pt(PPh 3)4 (2.5 mol%) under mild conditions. The effects of catalyst loading, solvent and temperature on the yield were also investigated. Furthermore, the trans-configuration of the product 5i was confirmed by X-ray diffraction analysis.
Relay catalysis: Enantioselective synthesis of cyclic benzo-fused homoallylic alcohols by chiral bronsted acid-catalyzed allylboration/ring closing metathesis
Fustero, Santos,Rodriguez, Elsa,Lazaro, Ruben,Herrera, Lidia,Catalan, Silvia,Barrio, Pablo
, p. 1058 - 1064 (2013/05/21)
Six- and seven-membered benzo-fused cyclic homoallylic alcohols can be readily synthesized by a tandem chiral Bronsted acid-catalyzed allyl (crotyl)boration/ring closing metathesis sequence performed under orthogonal relay catalysis conditions. Excellent enantio- and diastereoselectivities are obtained in most of the cases. In addition, the parent crotylboration/RCM process is also described. The required substrates, ortho-vinylbenzaldehydes, are readily available in one step from commercially available starting materials. Both catalysts and reactants are also available from commercial suppliers. The reaction shows broad functional group compatibility and is also suitable for heteroaromatic substrates. Substitution at any position of the aromatic ring is tolerated; however, substitution at position 6 results in a substantial drop in enantioselectivity. Copyright
Copper-catalyzed asymmetric ring-opening reaction of oxabenzonorbornadienes with Grignard and aluminum reagents
Millet, Renauds,Gremaud, Ludovic,Bernardez, Tania,Palais, Laetitia,Alexakis, Alexandre
experimental part, p. 2101 - 2112 (2009/12/31)
A highly enantioselective method for the copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand has been developed. The same reaction with Grignard reagents is also reported. A wide range of alky
