146174-55-2

Upstream product

• 146174-47-2 2-hydroxy-5-isopropyl-4-(4-tolylsulfonyl)tetrahydrofuran 
• 3185-99-7 Methyl p-tolyl sulfone 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 60682-95-3 1-(diethoxyphosphorylmethylsulfonyl)-4-methylbenzene 
• 177213-26-2 (E)-1-((3-(benzyloxy)prop-1-en-1-yl)sulfonyl)-4-methylbenzene 
• 185811-88-5 6-benzyloxy-2-methyl-4-(4-tolylsulfonyl)-5-hexen-3-ol 
• 154581-58-5 (E/Z)-3-benzyloxy-1-(4-tolylsulfonyl)-2-propene 
• 10154-76-4 3-(toluene-4-sulfonyl)propionic acid 
• 78-84-2 isobutyraldehyde 

Relevant academic research and scientific papers

(Alkoxyallyl)sulfones as enal β-anion equivalents. Synthesis of 5-substituted 2(5H)-furanones

2(5H)-Furanones 14 may be prepared in a four-step sequence starting from (alkoxyallyl)sulfone 10 and aldehydes.

Lithiated 3-Tosylpropanal and 4-Tosyl-2-butanone Dimethyl Acetals as β-Acylvinyl Anion Equivalents for the Synthesis of Unsaturated 1,4-Dicarbonyl Compound and α,β-Butenolides

The lithiation of 1,1-dimethoxy-3-tosyllpropane (7a) and 2,2-dimethoxy-4-tosylbutane (7b) followed by reaction with acyl chlorides affords, after p-toluenesulfinic acid elimination, ene-1,4-dicarbonyl compounds in a stereoselective manner.In the case of compound 7a, derived from acrolein, sequential monolithiation and reaction with carbonyl compounds give cyclic acetals, which after oxidation and elimination of p-toluenesulfinic acid are transformed into α,β-butenolides.

Lithium 3-Lithio-3-tosylalkanoates: β-Acylvinyl Anion Equivalents of β-Lithiated α,β-Unsaturated Carboxylic Acids

The dilithiation of β-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 deg C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11.They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12.When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoroacetic anhydride and base-promoted elimination α,β-butenolides are obtained.This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci).The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicycloundec-7-ene (DBU) afford α,β- and/or β,γ-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively.The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

Lithium 3-lithio-3-tosylpropanoate: A useful α-tosylated homoenolate anion

Lithium 3-lithio-3-tosylpropanoate prepared by dilithiation of 3-tosylpropanoic acid with n-butyllithium at -78°C, reacts with different electrophiles yielding the expected 3-functionalized tosylated propanoic acids. When carbonyl compounds are used as electrophiles the corresponding α,β-butenolides are prepared directly.

1-Benzyloxy-3-(p-tolylsulfonyl)propene as an acrolein β-anion equivalent. Synthesis of 4-substituted 2-butenolides

Lithiation of 1-benzyloxy-3-(p-tolylsulfonyl)propene 6 and reaction with aldehydes give alcohols 7. Sequential hydrolysis-cyclization, oxidation and DBU-mediated elimination of dine elements of p-TolSO2H gives 4-substituted 2-butenolides 10 in good overall yield.