99268-86-7

Upstream product

• 19978-32-6 3-bromo-2H-pyran-2-one 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 108329-99-3 3-(Toluene-4-sulfinyl)-5,6-dihydro-pyran-2-one 
• 504-31-4 pyran-2-one 
• 98061-54-2 3-(p-tolylthio)-2-pyrone 

Downstream Products

• 110474-22-1 (1R,4R,8R)-8-Methylsulfanyl-4-(toluene-4-sulfinyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one 
• 110474-17-4 (1S,4R,8R)-8-Ethoxy-4-(toluene-4-sulfinyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one 
• 110474-17-4 (1S,4R,8S)-8-Ethoxy-4-(toluene-4-sulfinyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one 
• 110474-24-3 (1S,4S,8S)-8-Phenylsulfanyl-4-(toluene-4-sulfinyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one 
• 69342-55-8 (3R,4R)-3-Hydroxy-4-(2-methoxy-ethoxymethoxy)-cyclohexa-1,5-dienecarboxylic acid methyl ester 
• 110474-23-2 (3R,4R,6R)-3,4-Dihydroxy-6-methylsulfanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 110474-33-4 (4S,5S,6S)-5,6-Dihydroxy-4-(2-methoxy-ethoxymethoxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 110474-25-4 (3S,4S,6S)-3,4-Dihydroxy-6-phenylsulfanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 110474-28-7 (3S,4S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,5-dienecarboxylic acid methyl ester 
• 110474-29-8 (3R,4R,6R)-3-Hydroxy-4-(2-methoxy-ethoxymethoxy)-6-phenylsulfanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 110474-30-1 (3R,4R,6R)-4-Hydroxy-3-(2-methoxy-ethoxymethoxy)-6-phenylsulfanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 110474-31-2 (3S,4S,6S)-6-Benzenesulfinyl-3-hydroxy-4-(2-methoxy-ethoxymethoxy)-cyclohex-1-enecarboxylic acid methyl ester 
• 110486-32-3 (3S,4S,6S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-phenylsulfanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 110474-26-5 (3R,4R,6R)-6-Benzenesulfinyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Highly Stereocontrolled Synthesis of Some Polyfunctionalized Cyclohexenes. A Short Formal Total Synthesis of (+/-)-Chorismic Acid

Lewis acid catalysis or high pressure is an effective means for promoting stereocontrolled 2 + 4 cycloaddition between pyrone sulfoxide 1 and vinyl ethers and vinyl thioethers.The bridged, bicyclic lactone cycloadducts are versatile synthons carrying much

AN ORGANOMETALLIC ROUTE TO (+/-)-3-p-TOLUENESULFINYL-2-PYRONE

3-Bromo-2-pyrone reacts with dimethylcopperlithium and then with p-tolyl p-toluenethiosulfonate to form 3-p-toluenethio-2-pyrone.Organocopper species are likely intermediates in this reaction.Oxidation of the sulfide produces (+/-)-3-p-toluenesulfinyl-2-pyrone.The overall process involves an important and useful umpolung, a reversal of reactivity at C(3) of the pyrone ring from an electrophilic center to a nucleophilic center.

3-Cuprio-2-pyrone: An Extraordinary Organocopper Reagent

3-Cuprio-2-pyrone (1) was prepared via Scheme I and was treated with a very wide variety of typically SN2- and SN1-reactive substrates as well as with typical acyl electrophiles.The only substrates that reacted via pyrone transfer we