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Phosphoramidite ligand information


A phosphoramidite ligand is any phosphorus-based ligand with the general formula P(OR1)(OR2)(NRR'). Chiral versions of these ligands, particularly those derived from the BINOL scaffold, are widely used in enantioselective synthesis. The application of phosphoramidites as effective monodentate ligands for transition metal catalysis was first reported by Dutch chemist Ben Feringa. The introduction of phosphoramidite ligands challenged the notion that high flexibility in the metal–ligand complex is detrimental for high stereocontrol.

General Structure of Phosphoramidite Ligand

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Phosphoramidite ligand

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A phosphoramidite ligand is any phosphorus-based ligand with the general formula P(OR1)(OR2)(NRR'). Chiral versions of these ligands, particularly those...

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Phosphoramidite

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analogs. Certain phosphoramidites are also used as monodentate chiral ligands in asymmetric synthesis. A large group of such ligands is derived from the...

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Asymmetric hydrogenation

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9%. A similar system using iridium(I) and a very closely related phosphoramidite ligand is effective for the asymmetric hydrogenation of pyrrolidine-type...

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Lewis acid catalysis

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taxane skeleton, uses a copper-based catalyst supported by a chiral phosphoramidite ligand for a conjugate carbonyl addition reaction. The second reaction...

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Diethyl tartrate

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"Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone". Angew. Chem. Int. Ed. 49 (11):...

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Biotinylation

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course of oligonucleotide synthesis by the phosphoramidite method using commercial biotin phosphoramidite. Upon the standard deprotection, the conjugates...

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Ben Feringa

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external chiral ligand, reduces the enantioselectivity. As BINOL-containing phosphoramidites have the properties of an intrinsic chiral ligand and simultaneously...

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Aminophosphine

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s)-Di(1-Phenylethyl) Aminophosphine. Scalable Protocols for the Syntheses of Phosphoramidite (Feringa) Ligands". Organic Syntheses. 85: 238–247. doi:10.15227/orgsyn.085...

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Acetonitrile

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dominant solvent used in oligonucleotide synthesis from nucleoside phosphoramidites. Industrially, it is used as a solvent for the manufacture of pharmaceuticals...

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Threose nucleic acid

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solid-phase synthesis using phosphoramidite chemistry. Methods for chemically synthesized TNA monomers (phosphoramidites and nucleoside triphosphates)...

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Nucleotide

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production of nucleotides. A purified nucleoside is protected to create a phosphoramidite, which can then be used to obtain analogues not found in nature and/or...

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Nucleic acid analogue

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synthesized enzymatically and can only be obtained synthetically using the phosphoramidite strategy or, for PNA, other methods of peptide synthesis.[citation...

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Oligonucleotide

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Oligonucleotides are chemically synthesized using building blocks, protected phosphoramidites of natural or chemically modified nucleosides or, to a lesser extent...

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Cluster of Excellence Frankfurt Macromolecular Complexes

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Jaumann EA, Scheffer U, Prisner TF, Göbel MW (2018). "A cytidine phosphoramidite with protected nitroxide spin label: synthesis of a full-length TAR...

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