30409-97-3

Upstream product

• 3709-18-0 2,2,5-trimethyl-1,3-dioxane-4,6-dione 
• 108-98-5 thiophenol 
• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 

Downstream Products

• 137960-30-6 3-hydroxy-2-methyl-5-phenyl-pentanethioic acid S-phenyl ester 
• 127422-22-4 3-hydroxy-2-methyl-5-phenyl-pentanethioic acid S-phenyl ester 

Relevant academic research and scientific papers

Synthesis of Monothiomalonates – Versatile Thioester Enolate Equivalents for C–C Bond Formations

Monothiomalonates (MTMs) are surrogates of thioester enolates that allow for stereoselective C–C bond formations under mild conditions and thereby afford access to synthetically versatile thioester derivatives. Here we present a straightforward synthetic route to MTMs that proceeds through nucleophilic ring-opening of Meldrum's acid derivatives followed by O-alkylation of the resulting malonic acid half thioesters with alkyl triflates or acetimidates as electrophiles. The method affords MTMs in overall yields of 34?–?92% and allows for variations of the oxo- and thioester moieties as well as the substituent at the C(α) position.

Bioinspired, base- and metal-free, mild decarboxylative aldol activation of malonic acid half thioesters under phase-transfer reaction conditions

Utilizing 'off the shelf' commercially available, cheap, small synthetic molecules that mimic the efficient mediation of important bioreactions utilized by Nature is not only highly sought after but also currently highly topical. This paper details our preliminary efforts at developing a unique base- and metal-free phase-transfer-mediated malonic acid thioester (MAHT) 'activation protocol' that efficiently generates (±)-β-thioesters. Our bioinspired aldol process is exceptionally mild, conducted under near neutral pH reaction conditions, does not require an inert, oxygen-free atmosphere or anhydrous reaction conditions and is highly atom-economic. Exemplifying the utility of our protocol, the synthesis of an array of structurally and functionally diverse (±)-β-hydroxy thioesters equipped with highly prized functionality, i.e., chlorine, bromine, fluorine, nitrile and nitro groups, is reported, as is the diastereoselective potential of this important reaction.

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

Catalytic enantioselective thioester aldol reactions that are compatible with protic functional groups

This communication reports highly enantioselective and diastereoselective methyl malonic acid half thioester (MeMAHT) aldol reactions that are compatible with protic functional groups and enolizable aldehydes, affording syn S-phenyl thiopropionates. Copyright