98674-79-4

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 4287, 1983 DOI: 10.1016/S0040-4039(00)88322-7

Upstream product

• 597-31-9 2,2-dimethyl-3-hydroxypropionaldehyde 
• 100-52-7 benzaldehyde 
• 78-84-2 isobutyraldehyde 
• 50-00-0 formaldehyd 
• 611-70-1 phenyl isopropyl ketone 
• 1750-74-9 2-benzoyl-2-methylpropanal 
• 598-26-5 dimethylketene 
• 98674-80-7 (R)-(-)-5,5-dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide 
• 90507-71-4 (R)-(-)-3-phenyl-3-hydroxy-2,2-dimethylpropanal 
• 88903-20-2 3-hydroxy-2,2-dimethyl-3-phenylpropanal 
• 1372861-85-2 (S)-2,2-dimethyl-1-phenyl-1,3-propanediol 3-O-pivaloate 
• 1273614-88-2 (S)-2,2-dimethyl-1-phenyl-1,3-propanediol 3-O-benzoate 
• 56010-63-0 2,2-dimethyl-3-hydroxy-1-phenylpropan-1-one 
• 133271-06-4 (S)-(+)-3-phenyl-3-hydroxy-2,2-dimethylpropanal 

Downstream Products

• 101499-58-5 1,3-diacetoxy-2,2-dimethyl-1-phenyl-propane 
• 24632-19-7 3,3-dimethyl-2-phenyloxetane 
• 121108-77-8 5,5-dimethyl-4-phenyl-1,3-dioxane 
• 98674-80-7 (R)-(-)-5,5-dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide 
• 98674-81-8 (S)-(+)-5,5-dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide 
• 100612-73-5 3-acetoxy-2,2-dimethyl-1-phenyl-propan-1-one 

Relevant academic research and scientific papers

3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions

This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.

Phosphine-oxide-catalyzed Enantioselective Cross-aldol Reactions of Aldehydes with Trichlorosilane as Lewis Acid Promoter

A hypervalent silicon complex between trichlorosilane and a chiral phosphine oxide acts as an effective Lewis acid mediator that successfully promotes highly enantioselective cross-aldol reactions between two aldehydes. The high yielding transformation is

Phosphinous Acid Platinum Complex as Robust Catalyst for Oxidation: Comparison with Palladium and Mechanistic Investigations

Secondary phosphine oxides proved to be effective preligands to stabilise a hydroxy-platinum based catalyst that allows the aerobic/anaerobic oxidation of challenging substrates. Kinetic comparisons showed that this system is more efficient and stable than previously reported similar palladium-based catalysts. A neutral platinum dimer bearing bridging hydroxy ligands has been isolated and fully characterised by X-ray diffraction and its involvement in the mechanism has been evidenced by mechanistic studies.

Exploiting Carbonyl Groups to Control Intermolecular Rhodium-Catalyzed Alkene and Alkyne Hydroacylation

Readily available β-carbonyl-substituted aldehydes are shown to be exceptional substrates for Rh-catalyzed intermolecular alkene and alkyne hydroacylation reactions. By using cationic rhodium catalysts incorporating bisphosphine ligands, efficient and selective reactions are achieved for β-amido, β-ester, and β-keto aldehyde substrates, providing a range of synthetically useful 1,3-dicarbonyl products in excellent yields. A correspondingly broad selection of alkenes and alkynes can be employed. For alkyne substrates, the use of a catalyst incorporating the Ampaphos ligand triggers a regioselectivity switch, allowing both linear and branched isomers to be prepared with high selectivity in an efficient manner. Structural data, confirming aldehyde chelation, and a proposed mechanism are provided.

A method for preparing chiral ring phosphoric acid (by machine translation)

The invention discloses a method for preparing chiral ring of phosphoric acid, the method comprises the following steps: a Isobutyraldehyde, aromatic aldehyde under the condition of chiral catalyst to catalyze the reaction generating chiral 3-aryl-3-hydroxy -2,2-dimethyl-propionaldehyde; chiral b 3-aryl-3-hydroxy -2,2-dimethyl propionic aldehyde reduction to obtain chiral 1-aryl -2,2-dimethyl -1,3-propylene glycol; c in methylene chloride under the conditions of reaction with phosphorus oxychloride to obtain chiral 4-aryl-2-chloro -5,5-dimethyl-2-oxo -1, 3, 2-dioxo-phosphorus heterocycle hexane chloride; in d hydrolysis under alkaline conditions, dyeworks generating chiral ring phosphoric acid. The high optical purity of the target product, the operation is simple, low cost, high yield, less pollution, belonging to the field of organic synthesis. (by machine translation)

Optical enrichment in enzyme-catalyzed resolution of 1-aryl-2,2-dimethyl-1,3-propanediols

Novozym 435 efficiently catalyzed the chemo-, regio-, and enantioselective transesterification of 1-aryl-2,2-dimethyl-1,3-propanediols in different organic solvents with vinyl acetate as the acetyl donor at room temperature. This enzyme-catalyzed chemical

Synthesis of highly-substituted enantiomerically pure allylboronic esters and investigation of their stereoselective addition to aldehydes

Diastereomerically pure allylboronates bearing the readily available tartrate derivative were obtained via sigmatropic rearrangement. Allyl additions were performed, and the influence of γ-disubstituted allylboronates was studied. Highly γ-substituted bor

Enantioselective evans-tishchenko reduction of β-hydroxyketone catalyzed by lithium binaphtholate

Lithium diphenylbinaphtholate catalyzed the enantioselective Evans-Tishchenko reduction of achiral β-hydroxyketones to afford monoacyl-protected 1,3-diols with high stereoselectivities. In the reaction of racemic β-hydroxyketones, kinetic optical resolution occurred in a highly stereoselective manner.

Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions

A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize β-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer.

Novel enantioselective direct aldol-type reaction promoted by a chiral phosphine oxide as an organocatalyst

Chiral phosphine oxide successfully catalyzed the direct aldol-type reactions of cyclohexanone derivatives and benzaldehyde derivatives in high stereoselectivities. The reaction mechanism involves the in situ formation of trichlorosilyl enol ethers. The present reaction could be extended to the cross-aldol reactions between two aldehydes.