Iridium-catalyzed asymmetric hydrogenation of imines in supercritical carbon dioxide using phosphite-type ligands

Lyubimov, S. E.; Rastorguev, E. A.; Petrovskii, P. V.; Kelbysheva, E. S.; Loim, N. M.; Davankov, V. A.

doi:10.1016/j.tetlet.2011.01.104

Cited by 23 publications

(8 citation statements)

References 25 publications

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“…1) that has been shown to be very efficient in the metallocomplex hydrogenation of dimethyl itaconate, enamides, and imines in organic solvents 26,27 and scCO 2 . 13,14,28 In the case of hydrogenation of (Z)-3a under optimized conditions (40 atm H 2 , 508C, 100 atm total pressure, HFIP as the co-solvent) only 49% ee was obtained despite the complete conversion in 3 h.…”

Section: Resultsmentioning

confidence: 99%

Application of a new amidophosphite ligand to Rh‐catalyzed asymmetric hydrogenation of β‐dehydroamino acid derivatives in supercritical carbon dioxide: Activation effect of protic co‐solvents

2011

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New chiral amidophosphite ligand was synthesized and tested in the Rh-catalyzed asymmetric hydrogenation of (Z)-β-(acylamino)acrylates in protic solvents and supercritical carbon dioxide (scCO(2) ) The catalytic performance is affected greatly by the acidity of the solvents. Better enantioselectivity (up to 88% ee) was achieved in scCO(2) containing 1,1,1,3,3,3-hexafluoro-2-propanol, compared to neat protic solvents.

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Section: Resultsmentioning

confidence: 99%

Application of a new amidophosphite ligand to Rh‐catalyzed asymmetric hydrogenation of β‐dehydroamino acid derivatives in supercritical carbon dioxide: Activation effect of protic co‐solvents

2011

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“…A catalyst loading of 1 mol % of the complex formed in situ from two equivalents of ligand 14 and [Ir(COD)2]BAr F 4 afforded the amine with a conversion of 82 % and 90% ee. 23 Once again, the use of fluorinated ligands was detrimental probably due to electronic effects. A catalyst loading of only 0.09 % of pre-formed iridium complex (Scheme 5c) with a bidentate ligand bearing fluorinated chains afforded full conversion but a moderate 80 % ee.…”

Section: Hydrogenation Reactionsmentioning

confidence: 99%

Homogeneous Metal-Based Catalysis in Supercritical Carbon Dioxide as Reaction Medium

2016

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Above 31.1 °C and 73.8 bar, carbon dioxide reaches the supercritical condition, being transformed into a fluid (scCO2) that has gained interest in the last decades as reaction medium for several transition metal-catalyzed organic transformations. The main feature of this fluid stands on its capability to dissolve large amounts of other gases such as hydrogen, carbon monoxide, ethylene or even methane and light alkanes. In this manner, very high concentrations of these reactants are available for catalysis. In this contribution a review of the main achievements of the use of transition metal complexes as catalysts in scCO2 is presented.

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“…F as the catalyst precursor in supercritical CO 2 (Scheme 39c). [88] Several aromatic imines were reduced in good to high enantioselectivities in short reaction times.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

“…Recently Lyubimov et al. reported another example of Ir‐catalyzed asymmetric hydrogenation of imines with ( R )‐PipPhos (( R )‐ 83 ) and [Ir(cod)] 2 BAr F as the catalyst precursor in supercritical CO 2 (Scheme c) 88. Several aromatic imines were reduced in good to high enantioselectivities in short reaction times.…”

Section: Iridium‐catalyzed Asymmetric Hydrogenation and Transfer Hydrmentioning

confidence: 99%

Enantioselective Synthesis of Alcohols and Amines by Iridium‐Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes

Bartoszewicz

Ahlsten

Martín‐Matute

2013

Chemistry A European J

162

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The preparation of chiral alcohols and amines by using iridium catalysis is reviewed. The methods presented include the reduction of ketones or imines by using hydrogen (hydrogenations), isopropanol, formic acid, or formate (transfer hydrogenations). Also dynamic and oxidative kinetic resolutions leading to chiral alcohols and amines are included. Selected literature reports from early contributions to December 2012 are discussed.

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Iridium-catalyzed asymmetric hydrogenation of imines in supercritical carbon dioxide using phosphite-type ligands

Cited by 23 publications

References 25 publications

Application of a new amidophosphite ligand to Rh‐catalyzed asymmetric hydrogenation of β‐dehydroamino acid derivatives in supercritical carbon dioxide: Activation effect of protic co‐solvents

Application of a new amidophosphite ligand to Rh‐catalyzed asymmetric hydrogenation of β‐dehydroamino acid derivatives in supercritical carbon dioxide: Activation effect of protic co‐solvents

Homogeneous Metal-Based Catalysis in Supercritical Carbon Dioxide as Reaction Medium

Enantioselective Synthesis of Alcohols and Amines by Iridium‐Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes

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