New phosphoramidite and phosphito-N chiral ligands based on 8-substituted quinolines and (S)-binaphthol; applications in the Cu-catalyzed enantioselective conjugate addition of diethylzinc to 2-cyclohexen-1-one

Arena, Carmela Grazia; Calabrò, GianPiero; Franciò, Giancarlo; Faraone, Felice

doi:10.1016/s0957-4166(00)00188-9

Cited by 29 publications

(12 citation statements)

References 30 publications

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“…[36,46,[66][67][68][69][70][71][72][73][74][75] These complementary and highyielding synthetic pathways towards phosphoramidites illustrate the modular framework of these ligands, a feature that has been applied to an easy and automated preparation of large ligand libraries (Figures 2 and 3). [76][77][78][79][80][81][82][83][84] Furthermore, the starting materials are cheap and available as enantiomerically pure compounds, [85] thus making the phosphoramidites easily accessible and low-priced chiral ligands. In terms of practicability it should be emphasized that many members of this ligand class are air-stable and do not require tedious procedures or handling under stringent inert conditions, as seen with several privileged phosphine ligands.…”

Section: Methodsmentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

638

340

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Asymmetric catalysis with transition-metal complexes is the basis for a vast array of stereoselective transformations and has changed the face of modern synthetic chemistry. Key to this success has been the design of chiral ligands to control the regio-, diastereo-, and enantioselectivity. Phosphoramidites have emerged as a highly versatile and readily accessible class of chiral ligands. Their modular structure enables the formation of ligand libraries and easy fine-tuning for a specific catalytic reaction. Phosphoramidites frequently show exceptional levels of stereocontrol, and their monodentate nature is essential in combinatorial catalysis, where a ligand-mixture approach is used. In this Review, recent developments in asymmetric catalysis with phosphoramidites used as ligands are discussed, with a focus on the formation of carbon-carbon and carbon-heteroatom bonds.

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Section: Methodsmentioning

confidence: 99%

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Teichert¹,

Feringa²

2010

Angew Chem Int Ed

638

340

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“…Argon 4.6 was purchased from Messer and traces of water and oxygen were removed with an M. Braun MB 100-HP apparatus. 1 H, 13 C and 31 P NMR spectra were recorded on a Bruker AV 600 (600, 150 and 243 MHz, respectively) or a Bruker DPX-300 spectrometer (300, 75 and 121 MHz, respectively). Chemical shifts (d) were referenced to residual solvent peaks ( 1 H NMR, 13 C NMR) or to external standard 85 % H 3 PO 4 ( 31 P NMR).…”

Section: Methodsmentioning

confidence: 99%

“…1 H, 13 C and 31 P NMR spectra were recorded on a Bruker AV 600 (600, 150 and 243 MHz, respectively) or a Bruker DPX-300 spectrometer (300, 75 and 121 MHz, respectively). Chemical shifts (d) were referenced to residual solvent peaks ( 1 H NMR, 13 C NMR) or to external standard 85 % H 3 PO 4 ( 31 P NMR). Mass spectra were recorded on a Varian 1200L Quadrupole GC-MS, Finnigan MAT 8200 (MS and HRMS-EI) or a Bruker FTICR-Apex III spectrometer (HRMS-ESI).…”

Section: Methodsmentioning

confidence: 99%

“…2 Hz,1 H;7.87 (d,J = 8.1 Hz,1 H;Ar),7.73 (d,J = 8.1 Hz,1 H;Ar),12 H;Ar),7.29 (m,1 H;Ar),7.24 (m,1 H;Ar),7.07 (d,J = 7.4 Hz,1 H;6.72 (m,1 H;Ar),6.62 (t,J = 7.5 Hz,1 H;Ar),5.34 (m,1 H;, 5.12 (d, J = 7. 3 Hz,1 H;NH),2.97 (m,1 H;2.74 (dt,J = 16.2,5.5 Hz,1 H;2.34 (m,1 H;, 2.08 ppm (m, 1 H; H-3); 13 (14), 316 (13), 290 (9), 258 (6), 238 (13), 222 (7), 221 (6), 183 (10) Ligand (R a ,S c )-13 a: A solution of phosphine 12 a (1.729 g, 3.898 mmol) in THF (40 mL) was cooled to À20 8C and phenyllithium (1 equiv, 2.12 mL, c = 1.84 m in di-n-butylether/cyclohexane, 30:70) was added slowly with a syringe. After complete addition, the reaction mixture was stirred for 1 h at 0 8C and then cooled to À20 8C.…”

Section: Methodsmentioning

confidence: 99%

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Quinaphos and Dihydro‐Quinaphos Phosphine–Phosphoramidite Ligands for Asymmetric Hydrogenation

Pullmann

Engendahl

Zhang

et al. 2010

Chemistry A European J

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New derivatives of the Quinaphos ligands and the related Dihydro-Quinaphos ligands based on the more flexible 1,2,3,4-tetrahydroquinoline backbone have been prepared and fully characterised. A general and straightforward separation protocol was devised, which allowed for the gram-scale isolation of the R(a),S(c) and S(a),R(c) diastereomers. These new phosphine-phosphoramidite ligands have been applied in the Rh-catalysed asymmetric hydrogenation of functionalised olefins with the achievement of excellent enantioselectivities (> or = 99%) in most cases and turnover frequency (TOF) values of up to > or = 20,000 h(-1). These results substantiate the practical utility of readily accessible Quinaphos-type ligands, which belong to the most active and selective category of ligands for Rh-catalysed hydrogenation known to date.

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“…[178,179] Application of these ligands in the copper-catalysed conjugate addition of diethylzinc to cyclohexenone resulted in a best enantioselection of 51% with 466.…”

Section: Pyridine N Donor Heteroatom Bound P Donormentioning

confidence: 98%

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

2004

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In this review, an attempt is made to systemise the ro √ le which bidentate phosphinamine (P,N) ligands play in asymmetric catalysis. The ligands will be classified, not by the reaction to which their metal complexes have been applied, but by the nature of their donor atoms. In this manner the development of ligand architectural design can be more easily monitored. The asymmetric transformations to which metal complexes of these ligands have been applied include among others, palladium-catalysed allylic substitutions, copper-catalysed 1,4-additions to enones and rhodiumcatalysed hydroboration of vinylarenes. Excellent enantioselectivities, regioselectivities and reactivities have been achieved in each of these processes.

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New phosphoramidite and phosphito-N chiral ligands based on 8-substituted quinolines and (S)-binaphthol; applications in the Cu-catalyzed enantioselective conjugate addition of diethylzinc to 2-cyclohexen-1-one

Cited by 29 publications

References 30 publications

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Phosphoramidites: Privileged Ligands in Asymmetric Catalysis

Quinaphos and Dihydro‐Quinaphos Phosphine–Phosphoramidite Ligands for Asymmetric Hydrogenation

The Development of Bidentate P,N Ligands for Asymmetric Catalysis

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