52411-61-7

Upstream product

• 20524-74-7 Dibutylthioborsaeure-phenylester 
• 100-52-7 benzaldehyde 
• 563-76-8 α-bromopropionyl bromide 
• 18245-72-2 S-phenylthiopropionate 
• 117481-61-5 tert-Butyl-dimethyl-((E)-1-phenylsulfanyl-propenyloxy)-silane 
• 120346-72-7 S-phenyl α-bromothiopropionate 
• 120346-76-1 S-phenyl α-iodothiopropionate 

Downstream Products

• 14366-91-7 syn-2-methyl-1-phenyl-1,3-propanediol 

Relevant academic research and scientific papers

Direct carbon-carbon bond formation via reductive soft enolization: A kinetically controlled syn-aldol addition of α-halo thioesters and enolizable aldehydes

The direct addition of enolizable aldehydes and α-halo thioesters to produce β-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-se

Ti-direct, powerful, stereoselective aldol-type additions of esters and thioesters to carbonyl compounds: Application to the synthesis and evaluation of lactone analogs of jasmone perfumes

An efficient TiCl4-Et3N or Bu3N-promoted aldol-type addition of phenyl and thiophenyl esters or thioaryl esters with aldehydes and ketones was performed (total 46 examples). The present method is advantageous from atom-economical and cost-effective viewpoints; good to excellent yields, moderate to good syn-selectivity, substrate variations, reagent availability, and simple procedures. Utilizing the present reaction as the key step, an efficient short synthesis of three lactone [2(5H)-furanone] analogs of jasmine perfumes was performed. Among them, the lactone analog of cis-jasmone had a unique perfume property (tabac). The Royal Society of Chemistry.

A facile and efficient direct aldol addition of simple thioesters

Simple thioesters undergo direct aldol addition to aldehydes in the presence of MgBr2·OEt2 and i-Pr2NEt using untreated, reagent-grade CH2Cl2 under atmospheric conditions. The reactions proceed extrem

Phosphine/Lewis acid mediated Reformatsky-type reaction of α-bromoketone or -thioester derivatives

The combination of (?-tolyl)3P/TiCl4 effectively promoted the Reformatsky-type reaction of α-bromoketone or -thioester derivatives with various aldehydes, and the corresponding β-hydroxy carbonyl compounds were obtained in good yield

Powerful stereoselective aldol-type additions of phenyl and phenylthio esters with aldehydes or ketones mediated by TiCl4/amine reagent

An efficient TiCl4/amine-promoted aldol-type addition of phenyl and phenylthio esters with aldehydes or ketones has been performed. The present method includes a practical merit from the green chemical viewpoint with regard to yields, variations of substrates, availability of reagents, and simple operations.

Diastereoselective Aldol Condensation of Silyl Ketene Acetal of 2-Pyridyl Thioester with Benzaldehyde

The TiCl4-mediated aldol reaction of the (E)-O-silyl ketene-O,S-acetal derived from 2-pyridyl thioester with benzaldehyde gave exclusively syn-aldol product.In contrast, BF3-mediated reaction afforded the corresponding anti-isomer as a major product.Chela

Diastereoselective aldol condensation of directly generated titanium enolates of activated esters

Simply generated (TiCl4, Et3N, -78°C) titanium enolates of some thioesters and α-thio substituted esters undergo aldol condensations with achiral and chiral aldehydes with low to high stereoselectivity. An 1H-NMR study of

STEREOSELECTIVE ALDOL CONDENSATIONS VIA ENOLBORONATES

Enolboronates, new enolates directly accessible from carbonyl compounds, exhibit extraordinary high erythro diastereoselection both with aliphatic and aromatic aldehydes.