444575-93-3

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 83859-26-1 lithium 2-methylphenoxide 
• 95-48-7 ortho-cresol 
• 21040-45-9 Cinnamyl acetate 
• 85669-63-2 (E)-cinnamyl diethyl phosphate 
• 4392-24-9 Cinnamyl bromide 
• 95932-32-4 tert-butyl (E)-cinnamyl carbonate 
• 86537-61-3 ethyl cinnamylcarbonate 
• 104-54-1 3-Phenylpropenol 
• 2687-12-9 cinnamyl chloride 
• 1448441-24-4 C₁₀H₁₀O₃ 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 1009-02-5 (2-methylphenoxy)trimethylsilane 

Downstream Products

• 180961-72-2 (R)-3-phenyl-2-(o-tolyloxy)propan-1-ol 
• 105314-52-1 (R)-tomoxetine 
• 115290-79-4 (R)-3-(2-methylphenoxy)-3-phenylprop-1-yl methanesulfonate 
• 1537223-06-5 (R)-3-phenyl-3-(2-methylphenoxy)propanal 

Relevant academic research and scientific papers

Enantio- And regioselective asymmetric allylic substitution using a chiral aminophosphinite ruthenium complex: an experimental and theoretical investigation

The design and synthesis of a new chiral aminophosphinite-ligated ruthenium complex is described. The ruthenium complex, [Ru(AMP)2(CH3CN)2][BPh4]2{AMP = (S)-tert-butyl 1-(diphenylphosphinooxy)-3-methylbutan-2-ylcarbamate}, has been found to catalyze nucleophilic addition of phenol and carboxylic acid to allyl chloride in a highly regioselective fashion with enantiomeric excess ranging from 12 to 90.

Catalyst-controlled wacker-type oxidation: Facile access to functionalized aldehydes

The aldehyde-selective oxidation of alkenes bearing diverse oxygen groups in the allylic and homoallylic position was accomplished with a nitrite-modified Wacker oxidation. Readily available oxygenated alkenes were oxidized in up to 88% aldehyde yield and as high as 97% aldehyde selectivity. The aldehyde-selective oxidation enabled the rapid, enantioselective synthesis of an important pharmaceutical agent, atomoxetine. Finally, the influence of proximal functional groups on this anti-Markovnikov reaction was explored, providing important preliminary mechanistic insight.

A chiral sulfoxide-ligated ruthenium complex for asymmetric catalysis: Enantio- and regioselective allylic substitution

The design and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols with good regio- and enantioselectivities.

Preparation of chiral ruthenium(iv) complexes and applications in regio- and enantioselective allylation of phenols

Facile preparations of chiral [Ru(Cp*)]- and [Ru(Cp′)]-based allyl complexes featuring N,O chelate derived from (+)-nopinone are described. Single crystal X-ray structural analysis of one complex revealed the preferential configuration of the ruthenium centre and the orientation of the unsymmetrical allylic substituent. Applications of these complexes in catalysis for nucleophilic allylic substitution allowed regio- and enantioselective formation of branched allyl ethers from phenols. The Royal Society of Chemistry.

Regio- and enantioselective O-allylation of phenol and alcohol catalyzed by a planar-chiral cyclopentadienyl ruthenium complex

(Chemical Equation Presented) Design of an asymmetric catalyst: The planar-chiral cyclopentadienyl ruthenium complex shown in the scheme effectively catalyzes the reactions of unsymmetrically substituted allyl halides with phenol and alcohol to give the corresponding branched allyl ethers with high regio- and enantioselectivity.

Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides

An enantioselective and regioselective iridium-catalyzed allylic etherification is described. The reaction of sodium and lithium aryloxides with achiral (E)-cinnamyl and terminal aliphatic allylic electrophiles in the presence of 2 mol % of an iridium-phosphoramidite complex provides chiral allylic aryl ethers in high yields and excellent levels of regio- and enantioselectivity. Lithium aryloxides containing a single substituent at an ortho, meta, or para position as well as sterically hindered phenoxides were tolerated. Reactions in THF displayed the most suitable balance of rate, regio-, and enantioselectivity. High ee's were also observed for the products from the reaction of alkyl (E)-allylic carbonates. Copyright

A stereospecific ruthenium-catalyzed allylic alkylation

Good regioselectivity and chirality transfer for aryl-substituted allyl units is achieved in allylic alkylations with a wide range of nucleophiles by using the highly active ruthenium catalyst 1. This method provides a route to antidepressants such as (-)-fluoxetine from (S)-ephedrine (see scheme; Cp* = η5-C5Me5, TBAT = tetrabutylammonium triphenyldifluorosilicate).