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Relevant academic research and scientific papers

Easy separation of Δ and Λ isomers of highly luminescent [IrIII]-cyclometalated complexes based on chiral phenol-oxazoline ancillary ligands

A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1-symmetric phenol-oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chromatography. The corresponding Δ and Λ helicities have been confirmed by CD spectroscopy and X-ray crystallography. Regarding the absorption and luminescence properties with unpolarized light, no significant difference between Δ and Λ isomers has been observed. A strong blue luminescence is observed for deaerated solutions of complexes 5 a and 5 b in CH3CN. Copyright

Alternatives to Phosphinooxazoline (t-BuPHOX) Ligands in the Metal-Catalyzed Hydrogenation of Minimally Functionalized Olefins and Cyclic β-Enamides

This study presents a new series of readily accessible iridium- and rhodium-phosphite/oxazoline catalytic systems that can efficiently hydrogenate, for the first time, both minimally functionalized olefins and functionalized olefins (62 examples in total) in high enantioselectivities (ees up to >99%) and conversions. The phosphite-oxazoline ligands, which are readily available in only two synthetic steps, are derived from previous privileged 4-alkyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline (PHOX) ligands by replacing the phosphine moiety by a biaryl phosphite group and/or the introduction of a methylene spacer between the oxazoline and the phenyl ring. The modular design of the ligands has given us the opportunity not only to overcome the limitations of the iridium-PHOX catalytic systems in the hydrogenation of minimally functionalized Z-olefins and 1,1-disubstituted olefins, but also to expand their use to unfunctionalized olefins containing other challenging scaffolds (e.g., exocyclic benzofused and triaryl-substituted olefins) and also to olefins with poorly coordinative groups (e.g., α,β-unsaturated lactams, lactones, alkenylboronic esters, etc.) with enantioselectivities typically >95% ee. Moreover, both enantiomers of the hydrogenation product could be obtained by simply changing the configuration of the biaryl phosphite moiety. Remarkably, the new catalytic systems also provided excellent enantioselectivities (up to 99% ee) in the asymmetric hydrogenation of another challenging class of olefins – the functionalized cyclic β-enamides. Again, both enantiomers of the reduced amides could be obtained by changing the metal from Ir to Rh. We also demonstrated that environmentally friendly propylene carbonate can be used with no loss of enantioselectivity. Another advantage of the new ligands over the PHOX ligands is that the best ligands are derived from the affordable (S)-phenylglycinol rather than from the expensive (S)-tert-leucinol. (Figure presented.).

A chloroform-containing chiral phosphine compound crystal and use

The invention provides a chiral phosphine crystal. The chemical formula of the chiral phosphine crystal is shown in the specification. A synthetic method of chiral phosphine comprises the following two steps: 1. subjecting 2-hydroxycyanophenyl (2-cyanophe

PHOX-Based Phosphite-Oxazoline Ligands for the Enantioselective Ir-Catalyzed Hydrogenation of Cyclic Β-Enamides

Simple Ir-PHOX-based phosphite-oxazoline catalysts have been successfully applied in the asymmetric hydrogenation of cyclic β-enamides providing better enantioselectivities than previous effective Ru and Rh catalysts. This protocol allows the synthesis of

Active versus passive substituent participation in the auxiliary-mediated asymmetric synthesis of an octahedral metal complex

Ambiguous chirality transfer: A surprising reversal of chirality transfer from carbon to metal is reported in the asymmetric synthesis of a chiral ruthenium complex, affording the metal-centered configuration or δ depending only on the chemical compositio

Syntheses and Crystal Structures of 4,5-Dihydro-2-(2'-hydroxyphenyl)oxazole-Containing Metal Complexes

The synthesis of the complexes 3 of various metals ligated to chiral 4,5-dihydro-2-(2'-oxidophenyl-χO)oxazoles-χN is described (Scheme).Three of them, i.e. 3a, 3e, and 3f containing Cu(II), Zn(II), and Ni(II), respectively, were analyzed by X-ray diffract