464178-73-2

Upstream product

• 64741-13-5 3-thiophenyl-3-sulfolene 

Downstream Products

• 464178-88-9 (S)-4-Benzenesulfonyl-3-methyl-cyclohexa-1,4-dienecarboxylic acid methyl ester 
• 464178-87-8 (S)-4-((S)-Benzenesulfinyl)-3-methyl-cyclohexa-1,4-dienecarboxylic acid methyl ester 
• 464178-84-5 [(S)-((Z)-Penta-1,3-diene)-3-sulfinyl]-benzene 

Relevant academic research and scientific papers

Asymmetric synthesis and applications of chiral 3-phenylsulfinyl-3-sulfolenes

The chiral 3-phenylsulfinyl-3-sulfolene 2 (S-form) was efficiently prepared in 92% ee by oxidation of sulfide 1 with Ti(O-i-Pr)4/(-)-DET/t-BuOOH (1:4:1) in toluene. Thermal desulfonylation of 2 gave chiral diene 3. Deprotonation of 2 by BuLi followed by the reaction with alkyl halides gave regiospecifically the C-2 alkylated 3-sulfolenes 4-8. Intramolecular Diels-Alder reactions of compounds 7 and 8 gave the bicyclic products 9-11. Thermal desulfonylation of 4 generated chiral dienyl sulfoxide 15, which underwent thermal and Lewis acid-catalyzed Diels-Alder reactions with good regio-, stereo- and enantioselectivity.