α-Phenylethylamine based chiral phospholidines; new agents for the determination of the enantiomeric excess of chiral alcohols, amines and thiols by means of 31P NMR

Hulst, Ron; Vries, N. K. De; Feringa, Bernard

doi:10.1016/0957-4166(94)80032-4

Cited by 156 publications

(106 citation statements)

References 21 publications

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“…8i (R)-MonoPhos was synthesized and isolated according to literature procedure. 17 The detailed synthesis procedure of ligand (S,S)-1a has been described in previous report. 9…”

Section: General Methodsmentioning

confidence: 99%

Nonlinear effects in the enantioselective 1,4-conjugate addition of diethylzinc to chalcone

Liang

Zheng

et al. 2003

Tetrahedron: Asymmetry

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“…8i (R)-MonoPhos was synthesized and isolated according to literature procedure. 17 The detailed synthesis procedure of ligand (S,S)-1a has been described in previous report. 9…”

Section: General Methodsmentioning

confidence: 99%

Nonlinear effects in the enantioselective 1,4-conjugate addition of diethylzinc to chalcone

Liang

Zheng

et al. 2003

Tetrahedron: Asymmetry

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“…[70] Early studies on this parent compound also highlighted the importance of using basis sets possessing polarization functions, [68] which are necessary on both phosphorus and nitrogen atoms to obtain the correct molecular Figure 1. Examples of widely used phosphoramidite ligands [1,2,3] derived from secondary amine. [79] Geometrical parameters are given at the B3LYP/ 6-31G(d) level.…”

Section: Resultsmentioning

confidence: 99%

“…Chiral phosphoramidite ligands widely used in asymmetric synthesis [1][2][3][4][5][6][7][8][9][10][11][12][13] (Fig. 1) possess a nitrogen atom in a trigonal planar conformation.…”

Section: Introductionmentioning

confidence: 99%

What governs nitrogen configuration in substituted aminophosphines?

Wodrich

Vargas

Morgantini

et al. 2008

J of Physical Organic Chem

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The trigonal planar geometry of the nitrogen atom in commonly used phosphoramidite ligands is not in line with the traditional valence shell electron pair repulsion (VSEPR) model. In this work, the effects governing nitrogen configuration in several substituted aminophosphines, A 2 PNB 2 (A or B ¼ H, F, Cl, Br, Me, OMe, BINOP), are examined using modern computational analytic tools. The electron delocalization descriptions provided by both electron localization function (ELF) and block localized wavefunction analysis support the proposed relationships between conformation and negative hyperconjugative interactions. In the parent H 2 PNH 2 , the pyramidal nitrogen configuration results from nitrogen lone pair electron donation into the s * P-H orbital. While enhanced effects are seen for F 2 PNMe 2 , placing highly electronegative fluorine substituents on nitrogen (i.e., Me 2 PNF 2 ) eliminates delocalization of the nitrogen lone pair. Understanding and quantifying these effects can lead to greater flexibility in designing new catalysts.

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“…All solvent transfers were carried out via cannula under positive argon pressure or by the use of gas-tight syringes. MonoPhos [11], [Rh(COD) 2 ]BF 4 [12], and a-acetamidoacrylic acid methyl ester [13] were prepared according to the literature procedure. The alumina used for the support was a neutral gamma-alumina obtained from Strem Chemicals and washed with ethanol to remove the fine particles before use.…”

Section: Immobilization and Characterization Of The Catalystmentioning

confidence: 99%

A Continuous-Flow System for Asymmetric Hydrogenation Using Supported Chiral Catalysts

Madarász¹,

Farkas²,

Balogh³

et al. 2011

J Flow Chem

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Highly active immobilized hydrogenation catalytic systems were used in the H-Cube ™ hydrogenation reactor. "In situ" produced [Rh(COD)((S)-MonoPhos) 2 ]BF 4 complex was immobilized on commercially available Al 2 O 3 and mesoporous Al 2 O 3 by means of phosphotungstic acid (PTA), respectively. The optimum reaction conditions were determined and studied at different temperature, pressure, and flow rate values. Furthermore, the effect of the substrate concentration, microstructure of the support, and the stability of the complex were investigated. A continuous-flow reaction system using a stationary-phase catalyst for the asymmetric hydrogenation of methyl acetamidoacrylate was developed and run continuously for 12 h with >99% conversion and 96-97% enantioselectivity.

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α-Phenylethylamine based chiral phospholidines; new agents for the determination of the enantiomeric excess of chiral alcohols, amines and thiols by means of 31P NMR

Cited by 156 publications

References 21 publications

Nonlinear effects in the enantioselective 1,4-conjugate addition of diethylzinc to chalcone

Nonlinear effects in the enantioselective 1,4-conjugate addition of diethylzinc to chalcone

What governs nitrogen configuration in substituted aminophosphines?

A Continuous-Flow System for Asymmetric Hydrogenation Using Supported Chiral Catalysts

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