138052-35-4

Upstream product

• 18245-72-2 S-phenylthiopropionate 
• 100-52-7 benzaldehyde 
• 117481-61-5 tert-Butyl-dimethyl-((E)-1-phenylsulfanyl-propenyloxy)-silane 
• 120346-76-1 S-phenyl α-iodothiopropionate 
• 120346-72-7 S-phenyl α-bromothiopropionate 
• 30409-97-3 rac-2-methyl-3-oxo-3-(phenylthio)propanoic acid 

Downstream Products

• 76549-05-8 methyl (2R,3R)-3-hydroxy-2-methyl-3-phenylpropanoate 
• 114418-46-1 1-Benzyl-3-methyl-4-phenyl-2-azetidinon 
• 151133-03-8 3-amino-2-methyl-3-phenyl-propionic acid methyl ester 
• 137960-34-0 (2R,3S)-3-Azido-2-methyl-3-phenyl-propionic acid methyl ester 
• 129823-46-7 (2R,3S)-3-Benzylamino-2-methyl-3-phenyl-propionic acid methyl ester 
• 137960-23-7 (3R,4S)-1-Allyl-3-methyl-4-phenyl-azetidin-2-one 
• 14366-91-7 syn-2-methyl-1-phenyl-1,3-propanediol 

Relevant academic research and scientific papers

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

Organocatalytic enantioselective decarboxylative aldol reaction of malonic acid half thioesters with aldehydes

Copycat: A highly enantioselective biomimetic aldol reaction of malonic acid half thioesters with a variety of aldehydes affords optically active β-hydroxy thioesters by employing the cinchona-derived sulfonamide organocatalyst 1. The synthetic utility of this protocol was demonstrated by performing formal syntheses of the antidepressants (R)-fluoxetine, (R)-tomoxetine, (-)-paroxetine, and (R)-duloxetine. Copyright

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.

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

The E/Z geometry of the enolate component determines face selection of the aldehyde component in chiral diazaborolidine-directed enantioselective aldol coupling

An analysis of the effect of enolate geometry on transition-state energy explains the stereochemistry of aldol reactions of acetate and propionate esters with aldehydes using as reagent the chiral diazaborolidine 1.

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 ALKENYLOXY DIALKYOXYBORANES: SYNTHETIC APPLICATIONS USING THIOESTERS.

A detailed investigation of the enolization of phenyl thiopropionate with ethylenechloroboronate (ECB) and diisopropylethylamine (DPEA) and the subsequent aldol condensations of these enolates was conducted.Alkenyloxy dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products.The thioester additions to chiral aldehydes were studied.Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used.The aldol products were transformed to known compounds for correlation.