474049-73-5

Usage

Uses

Used in Pharmaceutical Industry:
(S,S)-(-)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane is used as a ligand in the pharmaceutical industry for asymmetric synthesis and catalysis reactions. Its chiral properties allow for the creation of enantiomerically pure compounds, which are essential in the development of single-enantiomer drugs with improved efficacy and reduced side effects.
Used in Academic Research:
In academic research, (S,S)-(-)-1-hydroxy-1-oxo-2,5-trans-diphenylphospholane is utilized for the development of new synthetic methodologies. Its unique reactivity and chiral nature make it a valuable tool in exploring novel chemical reactions and creating innovative synthetic pathways for complex molecules.

Upstream product

• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 1428255-91-7 (2R,5R)-1-diethylamino-1-oxo-2,5-diphenylphospholane 
• 1159633-65-4 (5R)-1-hydroxy-1-oxo-2,5-diphenyl-4,5-dihydro-1H-phosphole 
• 88123-43-7 (E,E)-1,4-dideutero-1,4-diphenyl-1,3-butadiene 
• 1159633-62-1 (1s,2R,5S)-1-(diethylamino)-2,5-diphenyl-2,5-dihydro-1H-phosphole 1-oxide 
• 1159633-63-2 (1R,5R)-1-diethylamino-1-oxo-2,5-diphenyl-4,5-dihydro-1H-phosphole 
• 474093-56-6 (S,S)-(-)-1-chloro-1-r-oxo-2-c,5-t-diphenylphospholane 
• 1285720-82-2 C₁₆H₁₈NOP 
• 1285720-83-3 C₂₄H₂₅N₂O₃P 
• 949575-77-3 (meso)-1-(dimethylamino)-2,5-diphenyl-2,5-dihydrophosphole 1-oxide 
• 226393-36-8 1-(N,N-dimethylamino)-1-r-oxo-2-t,5-t-diphenylphospholane 
• 226393-31-3 1-(N,N-dimethylamino)-1-r-oxo-2-t,5-t-diphenylphosphol-3-ene 

Downstream Products

• 474093-56-6 (S,S)-(-)-1-chloro-1-r-oxo-2-c,5-t-diphenylphospholane 
• 1285720-83-3 C₂₄H₂₅N₂O₃P 
• 1285720-84-4 C₂₄H₂₄N₃O₅P 
• 1285720-85-5 C₂₄H₂₄FN₂O₃P 
• 1285720-86-6 C₂₄H₂₄FN₂O₃P 
• 1285720-87-7 C₂₄H₂₄BrN₂O₃P 
• 1285720-88-8 C₂₄H₂₄BrN₂O₃P 
• 1285720-89-9 C₂₂H₂₃N₂O₄P 
• 1285720-90-2 C₂₅H₂₇N₂O₃P 
• 1285720-91-3 C₂₅H₂₇N₂O₃P 
• 1285720-92-4 C₂₅H₂₇N₂O₄P 
• 1285720-93-5 C₂₂H₂₉N₂O₃P 

Relevant academic research and scientific papers

Group-Assisted Purification (GAP) Chemistry for the Synthesis of Velcade via Asymmetric Borylation of N-Phosphinylimines

A new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine's synthesis and in the asymmetric borylatio

Organocatalytic stereoisomerization versus alkene isomerization: Catalytic asymmetric synthesis of 1-hydroxy-trans -2,5-diphenylphospholane 1-oxide

The potential for an organocatalytic asymmetric stereoisomerization or alkene isomerization as atom-economic reaction with minimal structural change was investigated. The McCormack cycloaddition of 1,4-diarylbuta-1,3-dienes with (dialkylamino)dichlorophosphane and aluminum trichloride gives meso-2,5-diaryl-1-(dialkylamino)-1-oxo-2,5-dihydro-1H-phospholes, which were identified as suitable substrates for asymmetric isomerization to (1R,5R)-2,5-diaryl-1-(dialkylamino)-1-oxo-4,5-dihydro-1H-phospholes in the presence of bifunctional organocatalysts (cinchona alkaloids, Takemoto catalyst) in up to 91% ee and quantitative yield. The substrate range and the mechanism of the catalysis were studied. The reaction involves proton abstraction by the base, but a primary deuterium KIE is absent. Enriched (1R,5R)-1-(diethylamino)- 1-oxo-2,5-diphenyl-4,5-dihydro-1H-phosphole was hydrolyzed to (5R)-1-hydroxy-1-oxo-2,5-diphenyl-4,5-dihydro-1H-phosphole, which was hydrogenated diastereoselectively under dissolving metal conditions to give (2R,5R)-1-hydroxy-1-oxo-2,5-diphenylphospholane (Fiaud's acid) in preference to meso-1-hydroxy-1-oxo-2,5-diphenylphospholane. An asymmetric catalytic total synthesis of Fiaud's acid, which is a building block for chiral phospholane synthesis, has been realized in five steps from thiophene, using nickel-catalyzed Wenkert arylation, McCormack cycloaddition, asymmetric dihydro-1H-phosphole isomerization, hydrolysis, and diastereo-selective hydrogenation. Georg Thieme Verlag Stuttgart New York.

N-Phosphinyl Imine Chemistry (I): Design and Synthesis of Novel N-Phosphinyl Imines and their Application to Asymmetric aza-Henry Reaction

Novel chiral N-phosphinamide and N-phosphinyl imines have been designed, synthesized and applied to asymmetric aza-Henry reaction to give excellent chemical yields (92%- quant.) and diastereoselectivity (91% to >99%de). The reaction showed a great substra

Ambient temperature hydrophosphination of internal, unactivated alkynes and allenyl phosphineoxides with phosphine borane complexes

[Chemical Equation Presented] Phosphine boranes have been found to hydrophosphinate Internal, unactivated alkynes at room temperature under basic conditions without the need for catalysts or radical initiators. The use of air-sensitive secondary phosphine

Synthesis of building blocks for the development of the SUPRAPhos ligand library and examples of their application in catalysis

We have previously introduced the SUPRAPhos ligand library, which is based on components that are self-assembled through nitrogen-zinc interactions, and report here an extension of this library, which widens the scope for application in asymmetric homogeneous catalysis. For example, we report the synthesis of phosphorus amidite appended porphyrins and building blocks with stereogenic centers at the phosphorus. With the new building blocks described in this paper we can form a 450-membered SUPRAPhos library, which is based on 45 building blocks (30 pyridyl phosphorus ligands and 15 complementary porphyrin-appended phosphorus ligands). Examples of the use of members of the library in the rhodium-catalyzed asymmetric hydroformylation of styrene are included. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Enantioselective hydrogenation with self-assembling rhodium phosphene catalysts: Influence of ligand structure and solvent

Three sets of new and related chiral phospholane and phosphepine ligands have been prepared for Rh-catalyzed enantioselective hydrogenation. The size and substitution pattern of the cyclic monophosphanes were varied. More importantly, the ligands differ in the nature of the heterocyclic group linked to the trivalent phosphorus atom: 2-pyridone or 2-alkoxypyridine. In the corresponding Rh complexes, the pyridone units of two monodentate P ligands can assemble by hydrogen bonding and form chelates. In contrast, synthetic precursors bearing alkoxypyridine appendages are not able to aggregate via intramolecular hydrogen bonds. The nature of self-assembly is dependent on the nature of the P ligand and the solvent used for the hydrogenation (CH 2Cl2 vs. MeOH). These features affect the rate of the reaction as well as the enantioselectivity, which varied in the range of 0-99 % ee Complexation studies and DFT calculations were performed to explain these differences.

Synthesis and first applications of a new family of chiral monophosphine ligand: 2,5-diphenylphosphospholanes

The cyclic phosphinic acid 1-hydroxy-1-r-oxo-2c,5-t-diphenylphospholane was synthesized and resolved into enantiomers through fractional crystallization of the quinine salts. The P-phenyl, P-methyl and P-benzyl tertiary phosphine oxides were obtained from

Enantiomerically pure 1,2,5-triphenylphospholane through the synthesis and resolution of the chiral trans-(2,5)-diphenylphospholanic acid

The synthesis and resolution of trans-(2,5)-diphenylphospholanic acid 7 is described. The phosphinic acid 7 was converted into optically active (1,2,5)-triphenylphospholane 5 which was used as a chiral ligand in Rh- catalyzed hydrogenation of N-acetyl deh