P‐Chiral Ligands

Bayardon, Jérôme; Jugé, Sylvain

doi:10.1002/9781118299715.ch12

Cited by 19 publications

(8 citation statements)

References 208 publications

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“…Boranophosphates, which have an isoelectronic relationship with phosphates, are useful in biochemical investigations. They also have potential utility as carriers of 10 B in boron neutron capture therapy for cancer treatment. We tried to develop new reagents for the synthesis of similar compounds.…”

Section: Synthesis Of Enantiopure Tetracoordinate Boron Compound and Stereochemistry Of Substitution Reactions At Boron Atommentioning

confidence: 99%

Synthesis and applications of high-performance P-chiral phosphine ligands

Imamoto

2021

Proc. Jpn. Acad., Ser. B

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Section: Synthesis Of Enantiopure Tetracoordinate Boron Compound and Stereochemistry Of Substitution Reactions At Boron Atommentioning

confidence: 99%

Synthesis and applications of high-performance P-chiral phosphine ligands

Imamoto

2021

Proc. Jpn. Acad., Ser. B

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“…Organophosphorus compounds are of considerable importance due to their applications as medicines , (antiviral and anticancer agents), agrochemicals (pesticides and herbicides), ligands in catalysis, , and industrial additives , (e.g., polymers and fire retardants). Classical syntheses of these compounds suffer from the use of stoichiometric additives, the need for protecting groups, and poor functional group tolerance.…”

Section: Introductionmentioning

confidence: 99%

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

Huke

Taylor

Argent

et al. 2021

ACS Sustainable Chem. Eng.

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A catalyst-free, low-solvent method for the hydrophosphinylation of isocyanates and isothiocyanates is reported. A range of phosphorus nucleophiles including secondary phosphine oxides HP(O)R 2 (R = Ph, i Pr), phosphites HP(O)(OR) 2 (R = Me, Et), and methyl phenylphosphinate were tested. The procedure tolerated isocyanates and isothiocyanates featuring a wide range of substituents and, with use of 4 equiv of 2-methyltetrahydrofuran (2-MeTHF), solid substrates can be utilized. Twenty-five compounds were prepared with improved functional group tolerance compared to previous methods allowing access to new compounds (16 are novel). Facile scale up and simple reaction conditions make this a straightforward and practical methodology for obtaining phosphorus analogues of ureas and thioureas, which are challenging to synthesize by other methods.

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“…One of the most common pathways for the generation of P -chirogenic phosphines was established by Jugé and co-workers. ,, In this method the chiral P -center is created by the assistance of (−)-ephedrine as stereoinductor (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

P-Chirogenic Xantphos Ligands and Related Ether Diphosphines: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation

et al. 2017

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A series of P-chirogenic Xantphos ligands and related diaryl ether diphosphines have been synthesized by a modification of the well-established Jugé method. The approach consists of the in situ deboranation of the chiral ephedrine-based phosphinite before the P–C coupling takes place. The stereochemical integrity of the stereocenters of the diphosphines during synthesis, long-time storage, and catalytic application was evaluated. In the rhodium-catalyzed asymmetric hydrogenation of isophorone as a model substrate for industrially relevant prostereogenic enones with some of the diphosphines, almost complete conversion, high chemoselectivity, and 96% ee were achieved.

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P‐Chiral Ligands

Cited by 19 publications

References 208 publications

Synthesis and applications of high-performance P-chiral phosphine ligands

Synthesis and applications of high-performance P-chiral phosphine ligands

Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates under Low-Added-Solvent Conditions

P-Chirogenic Xantphos Ligands and Related Ether Diphosphines: Synthesis and Application in Rhodium-Catalyzed Asymmetric Hydrogenation

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