212067-72-6

Upstream product

• 177547-60-3 (1R,2R,3R,S_S)-2-<3'-(Tolyl-p-sulfinyl)-2'-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene 
• 14371-10-9 (E)-3-phenylpropenal 
• 542-92-7 cyclopenta-1,3-diene 
• 177547-56-7 (S_S)-trans-2-Cinnamoyl-3-(tolyl-p-sulfinyl)furan 
• 211931-20-3 (1R/1S,S_S)-1-<3-(p-tolylsulfinyl)-2-furyl>-trans-cinnamyl alcohol 
• 177547-58-9 (1S,2R,3R,4R,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene 

Relevant academic research and scientific papers

Remote asymmetric induction in lewis acid-catalyzed Diels-Alder reaction of α,β-unsaturated enones having a chiral sulfinyl-substituted, 5-membered aromatic heterocycle

Two types of chiral sulfoxides as Diels-Alder dienophiles were synthesized and high levels of diastereoselectivity were observed in cycloadditions. 2-Furyl and 2-thienyl α,β-enones, bearing a chiral sulfinyl group in the heterocycle, served as efficient dienophiles in Diels-Alder reactions, where the catalytic use of aluminium chloride or a lanthanide triflate effected the cycloaddition with cyclopentadiene affording the endo adduct with high diastereoselectivity, ranging from 91% to 98%.

A highly asymmetric, Lewis acid-catalysed Diels-Alder reaction using optically active 2-(3-tolyl-p-sulfinyl)furyl α,β-unsaturated ketones as a dienophile

The Diels-Alder reaction of chiral 2-(3-tolyl-p-sulfinyl)furyl α,β-unsaturated ketones 3 and 4 with cyclopentadiene in the presence of a Lewis acid proceeds smoothly to give the corresponding endo adducts 5a and 6a, respectively, in excellent yield with high diastereoselectivity.