Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamines and Imines

Xie, Jian‐Hua; Zhu, Shou‐Fei; Zhou, Qi‐Lin

doi:10.1021/cr100218m

Cited by 1,023 publications

(293 citation statements)

References 248 publications

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“…The crude product was purified by flash chromatography on silica gel, hexane:dichloromethane (2:1) to yield 4 (6.84 g, 84%) as large white crystals. (6). A suspension of 5 (4.51 g, 10.8 mmol) and palladium acetate (10% on carbon, 1.10 g, 1.08 mmol) in ethyl acetate (25 mL) was heated under hydrogen gas (1 atm) at 45 °C for 3 h. After filtration through Celite, the solvent was evaporated under reduced pressure to afford 6 (3.42 g, 96%) as a slightly yellow solid, which was used without further purification.…”

Section: Preparations Of Phosphinoxides 1-3mentioning

confidence: 99%

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Synthesis of New BINAP-Based Aminophosphines and Their 31P-NMR Spectroscopy

et al. 2013

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BINAP aminophosphines are prevalent N,P-bidentate, chiral ligands for asymmetric catalysis. While modification via the BINAP-nitrogen linkage is well explored and has provided a diverse body of derivatives, modification of the other substituents of the phosphorous center is another avenue in generating new congeners of this important class of chiral ligands. Herein reported are new BINAP aryl aminophosphines with electron rich or deficient substituents on the aryl rings. This scalable synthesis converted readily available starting material, (S)-BINOL, to a key intermediate (S)-NOBIN, from which the final chiral aminophosphines were prepared via a palladium-catalyzed, phosphonylation reaction. The aryl substituents are able to modify the electronic properties of the phosphorous center as indicated by the range of 31 P-NMR shifts of these new ligands. A computational analysis was performed to linearly quantitate contributions to the 31 P-NMR shifts from both resonance and field effects of the substituents. This correlation may be useful for designing and preparing other related aminophosphines with varying ligand properties.

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Section: Preparations Of Phosphinoxides 1-3mentioning

confidence: 99%

“…Bidentate N,P-ligands are particularly effective and have been investigated extensively [5][6][7][8]. Among the variety of chiral backbones,…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New BINAP-Based Aminophosphines and Their 31P-NMR Spectroscopy

et al. 2013

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“…It is well known that chiral iridium catalysts are applicable to the enantioselective hydrogenation of imines [71]. Recently, it has been shown that ketones, including ,β-unsaturated ketones, are also efficiently hydrogenated when iridium catalysts are used with P,N-ligands [72,73].…”

Section: Hydrogenation Of Simple Ketonesmentioning

confidence: 99%

Asymmetric Hydrogenation

Imamoto¹

2012

Hydrogenation

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“…The imine moieties are important intermediates and versatile starting materials for the synthesis of chiral amines [23,24], pyrimidine derivatives [25], phenylhydrazones [26,27], Mannich bases [28], indoles [29], quinoxalines [30], imidazoles [31], amino triphenylmethanes [32], Michael adducts [33], allyl products [34], optically active α-alkyl aldehydes [35,36] by hydrogenation [37], nucleophilic addition with organometallics [38] and cycloaddition reaction [39]. Many reagents have been used for the synthesis of optically active imines such as solid super acids, K-10 montmorillonite [40,41], Tandam catalysts [42], MnO 2 [43], CaO [44], ZnCl 2 [23,24], MgSO 4 -PPTS [26,27], alumina [45], Ti(OR) 4 [46], CuCl [47], MCM-41-SO 3 nanocatalyst [48], P 2 O 5 -SiO 2 [49] promoted by microwave irradiation [43], Cinchona alkaloid-thiourea [50], Infrared [51,52] and ultrasound radiation [53].…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Synthesis and Spectral Linearity of Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2<i>H</i>-cyclopenta[b]thiophene-3-carboxamides

Thirunarayanan

Sekar²

2013

ILCPA

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Some(E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta [b]thiophene-3-carboxamide derivatives have been synthesized by SiO 2 :H 3 PO 4 catalyzed solventfree condensation of 2-amino-N-(3-chloro-4-fluorophenyl)-hexahydro-2H-cyclopenta [b]thiophene-3-carboxamide and various substituted benzaldehydes in microwave irradiation. The yield of the iminecarboximido derivatives has been found to be more than 85 %. The purity of all imine-carboximido derivatives has been checked using their physical constants and spectral data. The spectral data of the iminecarboximido derivatives such as infrared ν (cm -1 ) of CO, NH, C-N, C-Cl, C-F, C=N, and the NMR chemical shifts (δ, ppm) of NH, CH, CO and C=N have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analysis, the effects of substituent on the above spectral group absorptions have been discussed.

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Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamines and Imines

Cited by 1,023 publications

References 248 publications

Synthesis of New BINAP-Based Aminophosphines and Their 31P-NMR Spectroscopy

Synthesis of New BINAP-Based Aminophosphines and Their 31P-NMR Spectroscopy

Asymmetric Hydrogenation

Solvent-Free Synthesis and Spectral Linearity of Some (E)-2-(substituted benzylideneamino)-N-(3-chloro-4-fluorophenyl)-hexahydro-2<i>H</i>-cyclopenta[b]thiophene-3-carboxamides

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