177547-60-3Relevant 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
Arai, Yoshitsugu,Masuda, Tsutomu,Masaki, Yukio
, p. 1078 - 1083 (2007/10/03)
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
Arai, Yoshitsugu,Masuda, Tsutomu,Masaki, Yukio,Shiro, Motoo
, p. 759 - 762 (2007/10/03)
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.
