26923-50-2

Upstream product

• 1374313-55-9 5-phenylpent-1-en-3-yl but-3-enoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 10186-22-8 6-(2-phenylethyl)tetrahydropyran-2-one 
• 172805-64-0 6-Phenethyl-3-phenylselanyl-tetrahydro-pyran-2-one 
• 89922-39-4 ethyl 2-(α-hydroxybenzyl)-3-butenoate 

Downstream Products

• 6507-91-1 (2Z,4E)-7-phenylhepta-2,4-dienoic acid 
• 172805-69-5 6-Ethoxy-2-phenethyl-3,6-dihydro-2H-pyran 
• 172805-65-1 6-Phenethyl-5,6-dihydro-2H-pyran-2-ol 
• 119239-93-9 4(S),6(S)-4-hydroxy-6-(2-phenylethyl)tetrahydropyran-2-one 
• 86117-01-3 (4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols

Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under

Enantioselective Redox-Divergent Chiral Phosphoric Acid Catalyzed Quinone Diels–Alder Reactions

An efficient enantioselective construction of tetrahydronaphthalene-1,4-diones as well as dihydronaphthalene-1,4-diols by a chiral phosphoric acid catalyzed quinone Diels–Alder reaction with dienecarbamates is reported. The nature of the protecting group on the diene is key to the success of achieving high enantioselectivity. The divergent “redox” selectivity is controlled by using an adequate amount of quinones. Reversible redox switching without erosion of enantioselectivity was possible from individual redox isomers.

αβ-Unsaturated δ-valerolactones through RCM-isomerization sequence

αβ-Unsaturated δ-lactones are accessible via a sequential ring-closing metathesis (RCM) double-bond migration reaction starting from butenoates of allyl alcohols. This approach proceeds efficiently with lower catalyst loadings and higher initial substrate concentrations compared to the alternative RCM of acrylates derived from homoallylic alcohols. Georg Thieme Verlag Stuttgart . New York.

The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols

A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.

New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes

The γ-adducts of homoallylic alcohols 3, derived from aldehydes via the usual reaction with common allylic metals 1, were converted to the corresponding α-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti-and syn

3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran. 1,3-Acyclic diastereoselection in reaction with MeOH and its application in the synthesis of a racemic mevinolin analog

3,4-Dehydro-2-hydroxy-6-(2-phenethyl)tetrahydropyran (6) and its dimer (7) both react with MeOH in the presence of a catalytic amount of conc. HCl to provide 2,4-bismethoxy-6-(2-phenylethyl)tetra-hydropyran with a decent level of 1,3-acyclic diastereoselection in favour of the 4,6-trans derivative (9a). The ratio of the arabino (9a) and xylo (9b) structures was an unprecedented 4:1. Models to account for the observed diastereoselectivity are discussed. Further transformation to the 2-oxo derivative and unmasking of the 4-OH function provide a rapid entry into a racemic mevinolin analog (14).