Category: 31886-57-4

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New chiral ferrocenylphosphines LB1-LB9 were designed and prepared through simple synthetic approaches. These air-stable ferrocenylphosphines were applied to promote asymmetric [3+2]-cycloaddition of Morita-Baylis-Hillman carbonates with maleimides, among which LB7 was shown to have good catalytic activity to afford the corresponding multifunctional cyclopentenes in up to 59% yield and up to 53% ee under mild reaction conditions. A plausible reaction mechanism was proposed.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Starting from (eta5-acetylcyclopentadienyl)(eta4-tetraphenylcyclobutadiene)cobalt(I), highly enantioselective (99 % ee) (S)-CBS catalysed ketone reduction followed by stereospecific alcohol-azide exchange, azide reduction and dimethyllation gave (R)-(eta5-alpha-N,N-dimethylaminoethylcyclopentadienyl)(eta4-tetraphenylcyclobutadiene) cobalt(I) (Arthurs? amine). This underwent highly diastereoselective cyclopalladation to give di-mu-acetate-bis-(R)-[(eta5-(Sp)-2-(alpha-N,N-dimethylaminoethyl)cyclopentadienyl, 1-C, N)(eta4-tetraphenylcyclobutadiene)cobalt(I)]dipalladium, and highly diastereoselective lithiation to give (R)-(eta5-(Sp)-1-(alpha-N,N-dimethylaminoethyl)-2-(diphenylphosphino)cyclopentadienyl)(eta4-tetraphenylcyclobutadiene)cobalt(I) (PPCA) following the addition as electrophile of chlorodiphenylphosphine. This PN-ligand was converted into (R)-(eta5-(Sp)-1-(alpha-dicyclohexylphosphinoethyl)-2-(diphenylphosphino)cyclopentadienyl)(eta4-tetraphenylcyclobutadiene)cobalt(I), a PP-ligand (Rossiphos), by stereospecific amine-phosphine exchange using HPCy2. These air-stable P?N and P?P complexes are the first examples of a new class of bulky planar chiral ligands for application in asymmetric catalysis.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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A rhodium-catalyzed regio- and enantioselective intermolecular allylation of malononitriles as masked acyl cyanides (MAC) with terminal and symmetrical internal allenes is reported. A RhI/Josiphos catalytic system combined with subsequent oxidative degradation of the primary adducts enables a straightforward access to alpha-branched, beta,gamma-unsaturated carbonyl compounds. The present protocol exhibits perfect atom economy in the allylation step and is characterized by a great functional group compatibility. Furthermore, the use of alpha-substituted malononitriles allowed for the construction of all-carbon quaternary centers.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Treatment of the alpha-dimethylamino[3]ferrocenophane system 3 with methyl iodide followed by dimesitylphosphine (Mes2PH) gave the alpha-(dimesitylphosphino)[3]ferrocenophane 5. This forms a frustrated Lewis pair [5/8] with B(C6F5)3 (8) that rapidly reacts with dihydrogen under ambient conditions to probably give the phosphonium cation/hydrido borate anion salt [5-H+/H-8-]. This, however, is unstable under the applied reaction conditions with regard to replacement of the newly formed phosphonium leaving group at the ferrocenophane a-position for hydride from the [HB(C6F5)3 -] counteranion to eventually yield the unfunctionalized [3]ferrocenophane product (10) and Mes2PH· B(C 6F5)3 (11) – both characterized by independent syntheses. Analogously, Ugi’s amine (6) was converted to (1-(dimesitylphosphino) -ethyl)ferrocene (7). The frustrated pair [7/8] consumes dihydrogen under similar conditions to yield the reduction products ethylferrocene (14) and Mes2PH · B(C6F5)3 (11).

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic, and their interactions with reaction intermediates and transition states. In an article, 31886-57-4, name is (S)-N,N-Dimethyl-1-ferrocenylethylamine, introducing its new discovery. Application of 31886-57-4

The invention discloses a formula (I) indicated by the Ugi’s amine and its derivatives of the synthesis method, the method to ferrocene and its derivatives as raw materials, obtained by reductive amination of racemic […], then racemic […] split by the resolving agent, to a primary amine of the optical isomer, optical isomer primary amine by alkylation or reductive amination reaction shall be stated Ugi’s amine and its derivatives. The chiral Ugi’s amine and its derivatives can be used for synthesizing a series of Josiphos such ferrocene diphosphine ligand, as various metal complex catalyst of chiral ligand, is preparing a pharmaceutical intermediate, agricultural chemicals important chiral catalyst ligand, in metal catalytic asymmetric reaction have a wide range of application, and is suitable for industrial scale production. The invention mild reaction conditions, cheap raw material, the synthetic route is simple, higher yield and chiral purity. (by machine translation)

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Ferrocenyltrithiocarbonates (I) are readily obtained by treating alpha-ferrocenylcarbinols (II) successively with sodium hydride, carbon disulfide and alkyl halide.Formation of I occurs by intramolecular nucleophilic displacement of oxygen by sulfur with retention of configuration.This is supported by the nature of the other products formed and by the X-ray structure determination of an optically active compound I, which was refined to R = 0.038.The title compound of R configuration was obtained from (R)-ferrocenylmethylmethanol.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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The invention discloses a (S)- 1 – ferrocene ethyl dimethylamine preparation process. In the preparation process, in order to acetyl ferrocene as raw materials, the use of metal Ir complex with a chiral ferrocenyl tridentate ligands L* The reaction complex as a catalyst, by asymmetric catalytic hydrogenation to obtain (S)- 1 – ferrocenyl ethanol, then acetylation, dimethylamine substituted reaction, to obtain (S)- 1 – ferrocene ethyl dimethylamine. With the traditional chiral separating method preparation (S)- 1 – ferrocene ethyl dimethylamine processes of the prior art, the invention has the advantages embodied in: mild reaction conditions, the operation is simple, stereoselectivity is good, high yield, production cycle is short, the amount “three wastes”, easy industrialization, having great value and social and economic benefits. (by machine translation)

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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pKb values for the ferrocenylamines, [(eta-C5H4(CH2)xNH2)FeC p] x=1, 2, 3; [(eta-C5H4CH2NHR)FeCp] R=Me, 4, Ph, 5; {[eta-C5H4CHR?NR2]FeCp} R?/R=H/Me, 6, R?/R=H/Ph, 7, Me/Me, 8;[{eta-C5H4CHRNMe2)2Fe] R=H 9, Me 10; [{1,2eta-C5H3(CH2NMe2)(PPh2)}FeCp] 11, {1,2eta-C5H3[CH(Me)NMe2](PR2}}Fe[eta-C5H4(PPh2)n] n=0, R=iPr 12, Ph 13, n=1, R=Me 14, are correlated with inductive, neighbouring group and steric effects. Corresponding salts have been synthesised. The pKb has a marked influence on their chemistry. Protonation competes with complexation but cis-PtCl2L2 L=1-3, 5, 7, and cis-Pt(N-N)Cl2 L=8, 9, have been characterised. Two reversible couples [Fc+A/FcA], [Fc+AH+/FcAH+] (A=amine function) and an irreversible oxidation/protonation of A are linked by a EECE mechanism, but potentials for the first two are independent of the amine and similar to ferrocene. Nucleophilic attack by ferrocenylamines at the nitrile, protonation and ligand substitution are all observed with cis-[PtCl2(NCR)2].

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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The effect of an electric field on the adsorption of oligopeptides and DNA on a ferromagnetic substrate magnetized perpendicular to the surface was investigated. The direction of the magnetic moment of the substrate defines different adsorption rates for different enantiomers, and the direction of the electric field, perpendicular to the surface, defines different adsorption rates depending on the direction of the dipole moment of the adsorbed molecules.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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The typical design of chiral electroactive materials involves attaching chiral pendants to an electroactive polyconjugated backbone and generally results in modest chirality manifestations. Discussed herein are electroactive chiral poly-heterocycles, where chirality is not external to the electroactive backbone but inherent to it, and results from a torsion generated by the periodic presence of atropisomeric, conjugatively active biheteroaromatic scaffolds, (3,3-bithianaphthene). As the stereogenic element coincides with the electroactive one, films of impressive chiroptical activity and outstanding enantiodiscrimination properties are obtained. Moreover, chirality manifestations can be finely and reversibly tuned by the electric potential, as progressive injection of holes forces the two thianaphthene rings to co-planarize to favor delocalization. Such deformations, revealed by CD spectroelectrochemistry, are elastic and reversible, thus suggesting a breathing system. A jolt upon recognition: Torsion in the electroactive backbone endows poly-heterocycle films with high chiroptical activity, which is reversibly tunable by the electric potential, and outstanding enantiorecognition capability with about 100 mV between two enantiomeric ferrocenyl amino probes, in any order, in alternating sequences, and as a racemate.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis