1075-05-4

Upstream product

• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 873-66-5 1-propenylbenzene 
• 637-50-3 1-phenylpropene 
• 103687-21-4 ((CH₃)3C₆H₂)2BCHLiCH₃ 
• 100-52-7 benzaldehyde 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 93-54-9 1-Phenyl-1-propanol 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 4436-22-0 1-phenylpropylene oxide 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 5650-40-8 (S)-2-hydroxypropiophenone 
• 37580-42-0 (E)-2-methyl-1-phenyl-1,3-butadiene 
• 1333259-97-4 (S,Z)-2-methyl-1-phenylbut-2-ene-1,4-diol 
• 827608-92-4 (S)-4,4,5,5-tetramethyl-2-(1-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-2-yl)-1,3,2-dioxaborolane 

Downstream Products

• 88196-06-9 (1S,2S)-1-phenyl-1,2-propanediol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 159992-91-3 2,2,4-trimethyl-5-phenyldioxolan 
• 159992-92-4 2,2,4-trimethyl-5-phenyldioxolan 
• 123485-24-5 (1R,2S)-1,2-diacetoxy-1-phenylpropane 
• 123485-26-7 (1S,2R)-1,2-diacetoxy-1-phenylpropane 
• 123485-25-6 (1R,2R)-1,2-diacetoxy-1-phenylpropane 

Relevant academic research and scientific papers

OsO4?streptavidin: A tunable hybrid catalyst for the enantioselective cis-dihydroxylation of olefins

Taking control: Selective catalysts for olefin dihydroxylation have been generated by the combination of apo-streptavidin and OsO4. Site-directed mutagenesis allows improvement of enantioselectivity and even inversion of enantiopreference in certain cases. Notably allyl phenyl sulfide and cis-β-methylstyrene were converted with unprecedented enantiomeric excess.

Modular monodentate oxaphospholane ligands: Utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes

Tune it up! Tunable, chiral, monodentate oxaphospholane ligands (termed OxaPhos) are highly effective in the Pt-catalyzed title reaction, providing the 1,4-addition products in enantiomer ratios approaching 99:1 (see scheme). In the presence of enantiomerically pure cis-iBu-OxaPhos, a catalyst loading of only 0.02 mol% [Pt(dba)3] was sufficient for effective reaction. pin=pinacolato, dba=dibenzylideneacetone.

Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 °C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

Concatenated catalytic asymmetric allene diboration/allylation/ functionalization

(Chemical Equation Presented) Palladium-catalyzed enantioselective diboration of prochiral allenes generates a reactive chiral allylboron intermediate which is a versatile reagent for the allylation of carbonyls. Experiments that improve the enantioselectivity of this process, examine the substrate scope, and are directed toward functionalization of the allylation intermediate are described.

Hindered organoboron groups in organic chemistry. 23. The interactions of dimesitylboron stabilised carbanions with aromatic ketones and aldehydes to give alkenes

Dimesitylboron stabilised carbanions react with diarylketones to give the corresponding alkenes in mild conditions with good yields. Reactions with aromatic aldehydes are more complex, but in all cases E-alkenes are available in good yields by trapping the intermediates with chlorotrimethylsilane followed by treatment with aq. HF/CH3CN. Treatment of the same intermediates with trifluoroacetic anhydride gives mainly the Z-alkenes. The design and mechanisms of these important processes are considered.

Oxidation of Alkenes with Aqueous Potassium Peroxymonosulfate and No Organic Solvent

Aqueous potassium peroxymonosulfate oxidizes water-immiscible alkenes at room temperature in the absence of organic solvent.Acidic (pH 6.7 with NaHCO3 enabled selective epoxidations of 2,3-dimethyl-2-butene, 1-methylcyclohexene, cyclohexene, styrene, and β-methylstyrene.The order of decreasing reactivity of alkenes was: 2,3-dimethyl-2-butene > 1-methylcyclohexene cyclohexene > cyclooctene > α-methylstyrene β-methylstyrene > styrene > p-methylstyrene > allylbenzene. 1-Octene and tetrachloroethylene did not react.Phase-transfer catalysts, a colloidal cationic polymer, and a cationic surfactant microemulsion had little effect on the reaction.

Stereoselectrive Syntheses of Ephedrine and Related 2-Aminoalcohols of High Optical Purity from Protected Cyanohydrins

Ephedrine and related optically active β-aminoalcohols can be prepared by zinc borohydride reduction of aryl O-protected magnesium imines and aryl α-hydroxyimimes which in turn are readily available from optically active cyanohydrins.

Synthesis of Optically Active 1-Phenyl-1,2-propanediol by Use of Baker's Yeast

Reduction of 1-phenyl-1,2-propanedione with baker's yeast afforded (1R,2S)-1-phenyl-1,2-propanediol in high chemical and optical yield. (1R,2S)-, (1R,2R)- and (1S,2S)-1,2-propanediols were also prepared via (1R)- or (2S)-α-ketols, which were obtained as intermediates of the above reaction.

Asymmetric Synthesis of Both Enantiomers of Tomoxetine and Fluoxetine. Selective Reduction of 2,3-Epoxycinnamyl Alcohol with Red-Al.

Both enantiomers of tomoxetine 7a,7b and fluoxetine 8a,8b (as their hydrochloride salts) have been synthetized from cinnamyl alkohol by asymmetric epoxidation, and their absolute configurations have been established.Optimal conditions for regioselective Red-Al reduction at C-2 of 2,3-epoxycinnamyl alcohol are discussed.

THE DIMESITYLBORON GROUP IN ORGANIC SYNTHESIS 7. A UNIQUE VARIANT OF THE BORON-WITTIG REACTION WHICH STEREOSELECTIVELY YIELDS 1,2-DIOLS.

Low temperature oxidation of the intermediates in the Wittig reactions of aryl aldehydes with carbanions stabilised with an adjacent dimesitylboron group leads stereoselectively to erythro-1,2-diols.The mechanistic implications for the boron-Wittig reactions are discussed.