21448-79-3

Upstream product

• 6057-79-0 (S)-(-)-t-butyl(phenyl)phosphine oxide 
• 538311-40-9 C₁₁H₁₇OP 
• 7621-16-1 (+/-)-tert-butylmethylphenylphosphine 
• 56598-35-7 diphenyl(tert-butyl)phosphine oxide 
• 917-54-4 methyllithium 
• 791-28-6 Triphenylphosphine oxide 
• 75-11-6 diiodomethane 
• 122888-71-5 tert-Butyl-phenyl-phosphinothioic acid S-tributylstannanylmethyl ester 
• 74-88-4 methyl iodide 
• 122888-80-6 (-)-t-butyl(methylthiomethyl)phenylphosphine oxide 
• 591-51-5 phenyllithium 
• 75213-01-3 t-BuPhP(O)Cl 
• 75-16-1 methylmagnesium bromide 
• 54100-47-9 (R)-(+)-tert-butylphenylphosphanylthioic acid 

Relevant academic research and scientific papers

Synthesis and properties of tert-butylphenylmethylene(chloro)phosphorane

The synthesis and properties of tert-butylphenylmethylene(chloro)phosphorane were described. The prepared chlorophosphorane reacted with alcohols and phenol with the formation of the corresponding phosphonium salts. Its reaction with carbonyl compounds le

Methylene insertion reactions of samarium carbenoids into boron-hydrogen and phosphorus-hydrogen bonds

A samarium carbenoid, generated from diiodomethane and samarium metal, reacts with phosphine-boranes to afford phosphine-monomethylboranein good yields. The P-H bonds of secondary phosphine-boranes or secondary phosphine oxides are subjected to methylene

Synthesis of Optically Active Phosphorus Compounds via Metal Phosphinites Generated by Reaction of Optically Active Selenophosphinates with Phenyllithium

Sequential treatment of optically active Se-benzyl t-butylphenylselenophosphinate with PhLi and then with electrophiles such as alkyl halides elemental selenium gave optically active phosphorus compounds in good chemical and optical yields with a retention of configuration at phosphorus atom, together with benzyl phenyl selenide.

BOM-Phosphinite as an Electrophilic P-Stereogenic Transfer Reagent for the Synthesis of Bulky Phosphines: Synthesis of tert-Butyl(3,5-di- tert-butylphenyl)BisP*

BOM-tert-butylmethylphosphinite borane is an efficient electrophilic P-stereogenic transfer reagent for the synthesis of bulky tertiary phosphines. The novel methodology relies on a one-pot deprotection/substitution on the trivalent phosphinite that takes place with very high stereospecificity. The potential of this strategy is demonstrated with the synthesis of a wide scope of tertiary phosphines in excellent enantiomeric excess. The methodology was applied to the synthesis of a bulky P-stereogenic BisP ligand analogue.

Stereoselectivity of Michael Addition of P(X)-H-Type Nucleophiles to Cyclohexen-1-ylphosphine Oxide: The Case of Base-Selective Transformation

Michael addition of phosphorus nucleophiles to the unsymmetrically substituted tert-butyl(1,4-cyclohexadien-3-yl)phosphine oxide and its derivatives has been described. The addition proceeds with the formation of the mixture of two isomeric products with good yield and diastereoselectivity. The reaction of tert-butyl(cyclohexen-1-yl)methylphosphine oxide with phosphorus nucleophiles is base sensitive and might afford two epimers which differ at one chirality center. The absolute configuration of the products has been assigned on the basis of conformational and 1H NMR analysis, and the mechanism of the reaction has been discussed. The Michael addition of phosphorus nucleophiles is postulated to proceed with or without consecutive epimerization of two α-carbanions.

Synthetic LMoO2 compounds have long been of keen interest both as structural and functional models for molybdoenzymes and in their own right as catalysts for a variety of oxygen atom-transfer (OAT) reactions. Investigations of their use as cata

Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery

Several dialkyl-arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL-derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl-phenyl-propyl-phosphine oxide were separated with (R,R)- or (S,S)-spiro-TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single-crystal X-ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X-ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro-TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents.

Enantiodivergent Formation of C-P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides

Phosphorus Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct from that of the Phosphorus-Sulfur Incorporation reagents previously disclosed. Here, the adaptable phosphorus(V) scaffold enables sequential addition of carbon nucleophiles to produce a variety of enantiopure C-P building blocks. Addition of three carbon nucleophiles to Π, followed by stereospecific reduction, affords useful P-chiral phosphines; introduction instead of a single methyl group reveals the first stereospecific synthesis of methylphosphonate oligonucleotide precursors. While both Π enantiomers are available, only one isomer is required - the order of nucleophile addition controls the absolute stereochemistry of the final product through a unique enantiodivergent design.

Aryl group - A leaving group in arylphosphine oxides

The treatment of triphenylphosphine oxide with organometallic reagents leads to the substitution of up to three phenyl substituents with the incoming carbon nucleophile. The replacement of the phenyl/aryl group in tertiary diarylalkylphosphine oxides or even aryldialkylphosphine oxides was also observed. Naphthyl-substituted phosphine oxides undergo Michael-type addition at the naphthyl group when treated with organolithium reagent.

Method for manufacturing a new dephosphorizing ligand homochiral (by machine translation)

Disclosed are methods for making chiral phosphorus ligands including chiral phosphines, chiral phosphine oxides, phosphonamides, and aminophosphines. The chiral phosphorus ligands prepared by the methods of the invention are useful as components of chiral catalysts, e.g., transition metal complexes.