7210-37-9

Upstream product

• 186581-53-3 diazomethane 
• 63741-24-2 α-(p-tolylsulfinyl) β-hydroxy β-phenyl n-butanoate de t-butyle 
• 3759-31-7 3-hydroxy-3-phenylbutanoic acid 
• 17430-98-7 [(1S)-1-cyclohexylethyl]amine 
• 880-65-9 (-)S β-hydroxy β-phenyl n-butanoate de methyle 
• 80039-42-5 (3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-yl 2-bromoacetate 
• 98-86-2 acetophenone 
• 4519-10-2 trichloro<(1-methoxyethenyl)oxy>silane 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 358-60-1 triethoxyfluorosilane 
• 591-51-5 phenyllithium 
• 67-56-1 methanol 
• 1070240-43-5 S-tert-butyl (R)-3-hydroxy-3-phenylbutanethioate 
• 1263176-31-3 (S)-methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate 

Downstream Products

• 880-65-9 (-)S β-hydroxy β-phenyl n-butanoate de methyle 

Relevant academic research and scientific papers

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

Synthesis of new bipyridine N,N′-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone

Abstract: Two methods for the synthesis of new axially chiral bipyridine N,N′-dioxides based on catalytic [2+2+2] cyclotrimerization of diynes with nitriles were developed. The N,N′-dioxides were used as catalysts in enantioselective allylation of benzaldehyde with allyltrichlorosilane and aldol reaction of trichlorosilyl ketene acetal of methyl acetate with acetophenone. Graphical abstract: [Figure not available: see fulltext.].

N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

Conjugate boration of β,β-disubstituted unsaturated esters: Asymmetric synthesis of functionalized chiral tertiary organoboronic esters

Challenging tertiary organoboronic esters containing a β-ester group were prepared enantioselectively via the asymmetric conjugate boration of β,β-disubstituted α,β-unsaturated esters with a copper-phosphine catalyst (see scheme). The functionalized organoboron derivatives can be utilized as a carbon nucleophile to form all-carbon quaternary centers. Copyright

Asymmetric Mukaiyama aldol reaction of nonactivated ketones catalyzed by allo-threonine-derived oxazaborolidinone

(Chemical Equation Presented) Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary β-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.

Catalytic enantioselective aldol reaction to ketones

An enantioselective aldol reaction between ketones and ketene silyl acetals is described using CuF-chiral phosphine as a catalyst. The key for high enantioselectivity was the development of a novel ligand derived from Taniaphos combined with the unique ac

New chiral bis(diphenylphospholane) ligands: Design, synthesis, and application to catalytic enantioselective aldol reaction to ketones

New chiral bidentate diphenylphospholanes were designed targeting a catalytic enantioselective aldol reaction to ketones. Ligands 5l and 5m having cis-2-butenyl and cyclopropyl groups at the linker part, respectively, were identified as effective chiral ligands for a CuF-catalyzed enantioselective aldol reaction to ketones. Catalysts prepared from CuF?3PPh 3?2EtOH and these ligands produced ketone aldol products with up to 66% ee, which is promising particularly for this extremely difficult and important catalytic enantioselective carbon-carbon bond forming reaction. The enantioselectivity was strongly dependent on the linker structure. Construction of a deep chiral pocket around the copper metal with stable bidentate chelation is the key to meaningful enantioinduction.

Lewis base catalyzed, enantioselective aldol addition of methyl trichlorosilyl ketene acetal to ketones

The catalytic enantioselective addition of an acetate enolate equivalent to ketones is described. Methyl trichlorosilyl ketene acetal reacts with a wide range of ketones in the presence of pyridine N-oxide to afford the aldol addition products in excellen

Catalytic, enantioselective aldol additions to ketones

Catalytic, enantioselective additions of a trichlorosilyl ketene acetal to ketones have been demonstrated. The trichlorosilyl enolate of methyl acetate undergoes a rapid and high-yielding aldol addition to a wide range of ketones (aromatic, olefinic, acet

Asymmetric Addition of Organometallic Reagents to Homochiral β-Ketoacetals

The diastereoselectivity of the carbonyl addition of organolithium reagents to β-keto acetals was examined.Addition of MeLi to β-keto acetal derived from Pd(II)-catalyzed acetalization of phenyl vinyl ketone with (R,R)-2,4-pentanediol gave (4R, 6R)-4,6-di