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• 61540-13-4 tert-butyl thiopropionate 
• 100-52-7 benzaldehyde 
• 76943-95-8 (E)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene 
• 76943-94-7 (Z)-1-(tert-butylthio)-1-trimethylsilyloxyprop-1-ene 
• 120425-01-6 (Z/E)-1-tert-butylthio-1-trimethylsililoxy-1-propene 
• 1247747-90-5 S-t-butylphenyl α-iodothiopropionate 
• 6004-44-0 prop-1-en-1-one 
• 43143-00-6 C₁₂H₂₇BS 
• 75-66-1 2-methylpropan-2-thiol 
• 97250-85-6 2-((Z)-1-tert-Butylsulfanyl-propenyloxy)-[1,3,2]dioxaborolane 
• 102146-11-2 1-tert-butylthio-1-(tert-butyldimethylsilyloxy)prop-1-ene 
• 97250-84-5 tert-Butyl-((E)-1-tert-butylsulfanyl-propenyloxy)-dimethyl-silane 

Relevant academic research and scientific papers

Gallium(III) triflate catalyzed diastereoselective mukaiyama aldol reaction by using low catalyst loadings

A mild method for the diastereoselective Mukaiyama aldol reaction is reported. By using a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%), the transformation proceeds efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. To the best of our knowledge, this is the first report of a metal triflate acting as a safe, bench-stable, and slow-releasing source of triflic acid for the Mukaiyama aldol reaction. A diastereoselective Mukaiyama aldol reaction was performed under mild conditions with a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%). The transformation proceeded efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. 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

Method for Performing Aldol Reaction in Water

An aldol reaction in an aqueous solution between an aldehyde represented by the following formula (I): [in-line-formulae]R—CHO??(I) [/in-line-formulae] (wherein R is a hydrocarbon group which may have an substituent), and a silicon enolate represented by

Aqueous asymmetric Mukaiyama aldol reaction catalyzed by chiral gallium Lewis acid with trost-type semi-crown ligands

The combination of Ga(OTf)3 with chiral semi-crown ligands (1a-e) generates highly effective chiral gallium Lewis acid catalysts for aqueous asymmetric aldol reactions of aromatic silyl enol ethers with aldehydes. A ligand-acceleration effect was observed. Water is essential for obtaining high diastereoselectivity and enantioselectivity. The p-phenyl substituent in aromatic silyl enol. ether (2 h) plays an important role and increases the enantioselectivity up to 95% ee. Although aliphatic silyl enol ethers provided low enantioselectivities and silylketene acetal is easily hydrolyzed in aqueous alcohol, the aldol reactions of silylketene thioacetal (12) with aldehydes in the presence of gallium-Lewis acid catalysts give the β-hydroxy thioester with reasonable yields and high diastereo- (up to 99:1) and enantioselectivities (up to 96% ee).

Lithium acetate-catalyzed aldol reaction between aldehyde and trimethylsilyl enolate in anhydrous or water-containing N,N-dimethylformamide

Lithium acetate (AcOLi)-catalyzed aldol reactions between trimethylsilyl enolates and aldehydes proceed smoothly in anhydrous DMF or pyridine to afford the corresponding aldols in good to high yields under weakly-basic conditions (Tables 1-5). This cataly

Catalytic asymmetric aldol reactions in aqueous media using chiral bis-pyridino-18-crown-6 - Rare earth metal triflate complexes

Catalytic asymmetric aldol reactions in aqueous media have been developed using Pr(OTf)3 and chiral bis-pyrdino-18-crown-6 1. In the asymmetric aldol reaction using rare earth metal triflates (RE(OTf)3) and 1, slight changes in the i

Catalytic use of a boron source for boron enolate mediated stereoselective aldol reactions in water

Use of boron enolates in water! Boron enolates can be generated and used for aldol reactions in water by using a catalytic amount of Ph2BOH (see scheme). This is the first example of a catalytic use of a boron enolates. The mechanism of the rea

Chemistry of enoxysilacyclobutanes: Highly selective uncatalyzed aldol additions

O-(Silacyclobutyl) ketene acetals derived from esters, thiol esters, and amides underwent facile aldol addition with a variety of aldehydes at room temperature without the need for catalysts. The uncatalyzed aldol addition reaction of O-(silacyclobutyl) ketene acetals displayed the following characteristics: (1) the rate of reaction was highly dependent on the spectator substituent on silicon and the geometry of the ketene acetal, (2) the O,O-ketene acetal of E configuration afforded the syn aldol products with high diastereoselectivity (93/7 to 99/1), (3) conjugated aldehydes reacted more rapidly than aliphatic aldehydes, and (4) the reaction was mildly sensitive to solvent. In addition, the aldol reaction was found to be efficiently catalyzed by metal alkoxides. Labeling experiments revealed that the thermal aldol reaction proceeds by direct intramolecular silicon group transfer, while the alkoxide-catalyzed version probably proceeds via in situ generated metal enolates. Computational modeling of the transition states suggests that the boat transition structures are preferred, supporting the observed syn selectivity of the thermal aldol reaction. Both thermal and alkoxide-catalyzed Michael additions were investigated, revealing a competition between 1,2- and 1,4-addition favoring the former.

The catalytic asymmetric aldol reaction of aldehydes with unsubstituted and monosubstituted silyl ketene acetals: Formation of anti-β-hydroxy-α-methyl esters

The title rection with unsubstituted and monosubstituted silyl ketene acetals proceeds with high enantioselectivity, and in the latter case good diastereoselectivity favoring the anti-β-hydroxy-α-methyl esters in all reported cases.

A CONVENIENT METHOD FOR GENERATION OF TIN(II) THIOESTER ENOLATE AND ITS REACTION WITH ALDEHYDE

Tin(II) enolates of thioesters are conveniently generated by the addition of stannous thiolates to ketenes.The tin(II) enolates thus formed react with aldehydes to afford the corresponding β-hydroxythioesters in a syn-selective manner.And this method is applied to an enantioselective formation of β-hydroxythioesters by the use of a chiral diamine as ligand.