259796-80-0Relevant academic research and scientific papers
Diels-Alder reactions with 2-(arylsulfinyl)-1,4-benzoquinones: Effect of aryl substitution on reactivity, chemoselectivity, and π-facial diastereoselectivity
Carreno, M. Carmen,Garcia Ruano, Jose L.,Urbano, Antonio,Remor, Cynthia Z.,Arroyo, Yolanda
, p. 453 - 458 (2007/10/03)
Diels-Alder reactions of (SS)-2-(2'-methoxynaphthylsulfinyl)-1,4- benzoquinone (1b), 2-(p-methoxyphenylsulfinyl)-1,4-benzoquinone (1c), and 2- (p-nitrophenylsulfinyl)-1,4-benzoquinone (1d) with cyclopentadiene are reported. These cycloadditions allowed the highly chemo- and stereoselective formation of both diastereoisomeric endo-adducts resulting from reaction on the unsubstituted double bond C5-C6 of quinones working under thermal and Eu(fod)3- or BF3 · OEt2-catalyzed conditions. The synthesis of endo- adduct [4aS*,5S*,8R*,8aR*,SS*]-9d resulting from cycloaddition on the substituted C2-C3 double bond was achieved in a chemo- and diastereoselective way from quinone 1d in the presence of ZnBr2. The reactivity and selectivity of the process proved to be dependent on the electron density of the arylsulfinyl group.
