603958-86-7Relevant academic research and scientific papers
Chiral ferrocene P, N ligand derivative and preparation method and application thereof
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Paragraph 0081-0091, (2021/02/10)
The invention aims to provide a chiral ferrocene P, N ligand derivative and a preparation method and application thereof. The preparation method comprises the following steps: adding a chiral ferrocene phosphine amine compound, an acetophenone compound, neutral Al2O3 and anhydrous MgSO4 into a reaction container, adding a reaction solvent under the protection of nitrogen, carrying out stirring reaction at 100-130 DEG C, carrying out suction filtration, carrying out reduced pressure distillation to remove the solvent, dissolving in ethanol, adding NaBH4, and carrying out reduced pressure concentration and chromatography after the reduction reaction is completed to obtain the chiral ferrocene P, N ligand derivative. The chiral ferrocene P, N ligand derivative prepared by the invention has the advantages of novel structure and fine and adjustable spatial stereoeffect and electronic effect, can be used for catalyzing asymmetric 1, 3 dipole cycloaddition reaction, and has the advantages ofhigh catalytic efficiency and high enantiomeric selectivity.
A class of α-amino acids-derived multifunctional amidophosphane precatalysts: application to the highly enantio- and diastereoselective silver(I)-catalyzed 1,3-dipolar cycloaddition reaction
Hou, Yihui,Zhou, Zhipeng,Liu, Pingle,Wang, Jiankang,Hou, Qinglin,Wen, Pushan,Wang, Haifei
, p. 930 - 938 (2017/07/11)
A class of multifunctional amidophosphanes derived from chiral α-amino acids have been developed with two amide bonds, a tertiary amine and a phosphine. In combination with Ag(I) salts, these amidophosphanes have been demonstrated as highly efficient multifunctional catalysts in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides as well as the three-component reaction of the α-iminoesters in situ generated. Under optimal conditions, highly functionalized endo-8 pyrrolidines were obtained with good to excellent yields (up to 99% yield) and enantioselectivities (up to 98% ee).
Asymmetric [3+2] cycloaddition of azomethine ylides catalyzed by silver(I) triflate with a chiral bipyrrolidine-derived phosphine ligand
Gu, Xin,Xu, Zhen-Jiang,Lo, Vanessa Kar-Yan,Che, Chi-Ming
, p. 3307 - 3314 (2013/01/15)
Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The AgOTf + L1 protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%). Georg Thieme Verlag Stuttgart.New York.
Asymmetric [3+2] cycloaddition of azomethine ylides catalyzed by silver(I) triflate with a chiral bipyrrolidine-derived phosphine ligand
Gu, Xin,Xu, Zhen-Jiang,Che, Chi-Ming,Lo, Vanessa Kar-Yan
, p. 3307 - 3314,8 (2012/12/12)
Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The AgOTf + L1 protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%).
A novel Fe(II)/diaryl prolinol catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkenes
Wu, Haisheng,Wang, Bo,Liu, Hongqiang,Wang, Lei
experimental part, p. 1210 - 1215 (2011/04/12)
A novel Fe(II)/diaryl prolinol catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alkenes has been developed. In the presence of FeCl2 (10 mol %) and α,α-bis(3,5- bistrifluoromethylphenyl)prolinol L1 (10 mol %), [3+2] cycl
A new chiral phosphine oxide ligand for enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides
Eroeksuez, Serap,Dogan, Oezdemir,Garner, Philip P.
experimental part, p. 2535 - 2541 (2011/02/22)
A new set of phosphorus-containing chiral ligands has been synthesized and used with silver(I) for the catalytic asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides. One of these ligands (POFAM6) was found to produce an effective catalyst f
Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine-phosphoramidite ligand having a stereogenic P-center
Yu, Sai-Bo,Hu, Xiang-Ping,Deng, Jun,Wang, Dao-Yong,Duan, Zheng-Chao,Zheng, Zhuo
experimental part, p. 621 - 625 (2009/08/15)
A series of chiral ferrocene-based phosphine-phosphoramidite ligands (PPFAPhos) have been employed in the Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with dimethyl maleate. The results showed that the ligand with a stereogenic P-ce
Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions
Najera, Carmen,de Gracia Retamosa,Sansano, Jose M.,Cozar, Abel de,Cossio, Fernando P.
experimental part, p. 2913 - 2923 (2009/07/11)
The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the experimentally observed high enantio- and endo-selectivity through a very asynchronous transition state.
CuI-Fesulphos complexes: efficient chiral catalysts for asymmetric 1,3-dipolar cycloaddition of azomethine ylides
Cabrera, Silvia,Arrayás, Ramón Gómez,Martín-Matute, Belén,Cossío, Fernando P.,Carretero, Juan C.
, p. 6587 - 6602 (2008/02/05)
The CuI-Fesulphos catalyst system (≤3 mol %) shows an excellent performance in the asymmetric 1,3-dipolar cycloaddition of azomethine ylides. High to very high levels of reactivity, endo/exo selectivity, and enantioselectivity (69->99% ee) are generally achieved with a very wide range of azomethine ylides and dipolarophiles. Based on experimental and computational studies data, a model that accounts for this high enantiocontrol is proposed.
Hydrogen-bonding directed reversal of enantioselectivity
Zeng, Wei,Chen, Guo-Ying,Zhou, Yong-Gui,Li, Yu-Xue
, p. 750 - 751 (2007/10/03)
A successful stereochemical reversal was achieved in AgOAc catalyzed [3+2] cycloaddition by the formation of hydrogen bonding between ligand and reactant. This strategy provides an efficient and convenient route to prepare both enantiomers of a chiral compound. DFT studies proposed a reasonable mechanism of the reversal of the enantioselectivity; hydrogen bonding changed the transition state. The strategy may provide some useful hints for ligand design. Copyright
