89996-91-8

Upstream product

• 29668-62-0 methyl 2-(diethoxyphosphoryl)propanoate 
• 34713-70-7 2-Phenylpropanal 
• 140184-84-5 2-Triphenylstannanyl-propionic acid methyl ester 
• 86581-80-8 diphenyl phosphinoxy-2-propionate de methyle 
• 67-56-1 methanol 
• 335239-86-6 Methanesulfonic acid (E)-1,1-difluoro-2-methyl-4-phenyl-pent-2-enyl ester 
• 335239-79-7 tert-butyl-[3,3-difluoro-2-methyl-1-(1-phenyl-ethyl)-allyloxy]-dimethyl-silane 
• 2605-68-7 methyl 2-(triphenylphosphoranylidene)propionate 
• 335239-71-9 3-(tert-butyl-dimethyl-silanyloxy)-4-phenyl-pentan-2-one 

Downstream Products

• 129098-84-6 (2R,3R,4R)-3-Hydroxy-2-methyl-4-phenyl-pentanoic acid methyl ester 
• 72691-75-9 Methyl (2S^*,3R^*,4R^*)-3-hydroxy-2-methyl-4-phenylvalerate 
• 72691-74-8 Methyl (2R^*,3S^*,4R^*)-3-hydroxy-2-methyl-4-phenylvalerate 
• 103189-26-0 2,3-anti-3,4-syn-methyl 3-hydroxy-2-methyl-4-phenylpentanoate 
• 136066-30-3 4-Methylene-5-(1-phenylethyl)-1,2-dioxolan-3-one 
• 612840-26-3 C₁₃H₁₆⁽²⁾H₂O₃S 
• 612840-29-6 C₁₂H₁₃⁽²⁾H₃ 
• 612840-23-0 C₁₂H₁₄⁽²⁾H₂O 
• 128999-76-8 methyl 3-hydroperoxy-2-methylene-4-phenylpentanecarboxylate 
• 128999-77-9 methyl 3-hydroperoxy-2-methylene-4-phenylpentanecarboxylate 
• 128999-79-1 (3R,4R)-3-Hydroxy-2-methylene-4-phenyl-pentanoic acid methyl ester 
• 128999-78-0 (3S,4R)-3-Hydroxy-2-methylene-4-phenyl-pentanoic acid methyl ester 
• 127909-82-4 2-Methyl-3-(1-phenyl-ethyl)-oxirane-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Intrazeolite photooxygenation of chiral alkenes. Control of facial selectivity by confinement and cation-π interactions

Depending on the nature of the substituents on the stereogenic carbon atom, the ene reaction of singlet oxygen with several chiral alkenes by confinement within thionin-supported zeolite NaY, may exhibit significant changes on facial selectivity by comparison to their photooxygenation reaction in solution. It is proposed that, apart from the conformational consequences as a result of the alkene confinement within the zeolite cavities, a synergism between Na+-π interactions and singlet oxygen-Na+ interactions plays a significant role in the transition states of ene hydroperoxidation. Within NaY, the diastereoselectivity may significantly depend on the site selectivity, as probed through specific deuterium labelling of trisubstituted alkenes bearing a gem-dimethyl group. In certain cases, a remote stereogenic centre relative to the reacting double bond may induce enhanced diastereoselection and regioselectivity.

Remarkable Change of the Diastereoselection in the Dye-Sensitized Ene Hydroperoxidation of Chiral Alkenes by Zeolite Confinement

(Equation presented) The ene reaction of singlet oxygen with chiral trisubstituted alkenes bearing an alkyl and a phenyl group at the stereogenic center is erythro diastereoselective in solution and threo diastereoselective if carried out within zeolite Na-Y. The change of the diastereoselection trend by zeolite confinement is attributed to a synergism of steric effects and cation-π interactions.

Mesyloxy-group migration as the stereoselective preparation method of various functionalized olefins and its reaction mechanism

It was demonstrated that mesylation of appropriate γ,γ-difluorinated allylic alcohols under usual conditions furnished the corresponding α,γ-difluorinated allylic mesylates, possibly by way of 1,3-mesyloxy-group migration after formation of the expected "normal" intermediates, γ,γ-difluorinated allylic mesylates. This rearrangement was conveniently applied to the construction of trisubstituted allylic alcohols, α,β-unsaturated esters, amides, or ketones in good to excellent chemical yields with exclusive E selectivities.

Carbonyl olefination with α-stannyl ester enolates: a new synthesis of α,β-unsaturated esters

The reaction of α-stannyl ester enolates with carbonyl compounds is described. α,β-Unsaturated esters are obtained in good yields.A reaction mechanism is proposed.

SYNTHESE STEREOSELECTIVE D'ESTERS α,β-ETHYLENIQUES α-METHYLES Z OU E PAR LA REACTION DE WITTIG-HORNER A PARTIR DE PHOSPHONATES OU D'OXYDES DE PHOSPHINE

The reaction of α-branched aldehydes with diethyl 1-carbomethoxyethyl phosphonate 1b in THF/nBuLi at low temperature leads stereoselectively to Z α-methyl α,β-unsaturated esters.From a linear aldehyde, the reaction is less stereoselective, while from α,β-unsaturated ones, the E isomers are predominantly formed in good yields.From diphenyl 1-carbomethoxyethyl phosphine oxide 2b, E α-methyl α,β-unsaturated esters are stereoselectively formed either in DMF/tBuOK or in phase transfer conditions, whatever the starting aldehyde is, also in good yields.This reagent can thus advantageously replace the corresponding P-ylid.In all cases, the reaction conditions are determined so that by-products formation is minimized.

NOUVEAUX REACTIFS PRECURSEURS D' OLEFINES TRISUBSTITUEES E : LES OXYDES DE PHOSPHINE.

From NMR data, phosphine oxides 4 show similarity to Pylids and give E trisubstituted olefins from saturated and unsaturated aldehydes.