Optically active transistion-metal complexes. 9.1 A general stereoselective route to a-chiral (R)-tricarbonyl (h6-ethylbenzene)chromium complexes. Novel organometallic phosphine catalysts for the asymmetric hydrovinylation reaction

doi:10.1021/OM990386Q

Paper

Optically active transistion-metal complexes. 9.1 A general stereoselective route to a-chiral (R)-tricarbonyl (h6-ethylbenzene)chromium complexes. Novel organometallic phosphine catalysts for the asymmetric hydrovinylation reaction

Published Sep 16, 1999 · U. Englert, R. Haerter, Daniela Vasen

Organometallics

Q1 SJR score

52

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Abstract

Treatment of (R)-[{a-(dimethylamino)ethyl}-?6-benzene]Cr(CO)3 with esters of chloroformic acid leads to stereoselective substitution of the dimethylamino group for a chloro substituent. The reaction can be extended to systems in which the chromium arene complex, after metalation, is diastereoselectively substituted in the ortho position with carbon and silicon electrophiles to generate planar chirality. The chloro group in turn can be replaced stereoselectively for various phosphorus, nitrogen, and oxygen nucleophiles. Both substitution reactions in the benzylic position proceed via retention of configuration. The addition of cyanide is not stereospecific. The phosphine derivatives are efficient catalysts for the enantioselective hydrovinylation of styrene to 3-phenyl-1-butene. X-ray crystal structures establish the absolute configuration of (R)-[(a-chloroethyl)?6-benzene]Cr(CO)3, (R)-[{a-(diphenylphosphanyl)ethyl}-?6-benzene]Cr(CO)3, and (pS,S)-[1-(a-cyanoethyl)-2-methyl-?6-benzene]Cr(CO)3.

Study Snapshot

This study demonstrates a general stereoselective route to a-chiral (R)-tricarbonyl (h6-ethylbenzene)chromium complexes, with potential applications in organic synthesis and catalysis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Optically active transistion-metal complexes. 9.1 A general stereoselective route to a-chiral (R)-tricarbonyl (h6-ethylbenzene)chromium complexes. Novel organometallic phosphine catalysts for the asymmetric hydrovinylation reaction

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References

Citations

Catalytic Asymmetric C–H Arylation of (η6-Arene)Chromium Complexes: Facile Access to Planar-Chiral Phosphines

This study presents a catalytic asymmetric direct C-H arylation of (6-arene)chromium complexes, providing facile access to planar-chiral compounds, which can easily be transformed into planar chiral mono- or diphosphines.

Ruthenacyclopentanes as Intermediates in the Regio- and Stereoselective Linear Codimerization of N-Vinylamides with Electron-Deficient Alkenes

Ruthenacyclopentanes can serve as intermediates in the linear codimerization of N-vinylamides with electron-deficient alkenes, enabling efficient and selective synthesis of linear alkenes.

Low-Pressure Cobalt-Catalyzed Enantioselective Hydrovinylation of Vinylarenes.

This study developed a low-pressure cobalt-catalyzed hydrovinylation protocol for enantioselective hydrolysis of vinylarenes with ethylene, enabling the conversion of diverse substrates with up to 99 % ee and complete regioselectivity.

Phosphine-olefin ligands based on a planar-chiral (π-arene)chromium scaffold: design, synthesis, and application in asymmetric catalysis.

Planar-chiral (-arene)chromium ligands show high performance in rhodium-catalyzed asymmetric reactions, with compound 3g showing excellent enantioselectivity and high yields.

Highly Efficient Catalytic Dimerization of Styrenes via Cationic Palladium(II) Complexes

Cationic palladium(II) complexes enable highly efficient head-to-tail dimerization of styrenes, providing a new economical CC bond forming method.

Gold(I)-catalyzed asymmetric induction of planar chirality by intramolecular nucleophilic addition to chromium-complexed alkynylarenes: asymmetric synthesis of planar chiral (1H-isochromene and 1,2-dihydroisoquinoline)chromium complexes.

Gold(I)-catalyzed asymmetric intramolecular cyclization of chromium-complexed alkynylarenes leads to the synthesis of planar chiral (1H-isochromene and 1,2-dihydroisoquinoline) chro

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Ethylene can be easily incorporated into transition-metal-catalyzed carbon-carbon bond-forming reactions, resulting in useful substituted alkenes at ambient pressure and temperature.

Metal catalysed hydrovinylation

Transition metal organometallic complexes can catalyze hydrovinylation to generate new stereogenic centers and functionalize vinyl compounds, with potential applications in various fields.