162060-46-0

Upstream product

• 134281-83-7 (+)-(S)-2-(p-tolylsulfinyl)cyclohexa-2,5-diene-1,4-dione 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 187592-86-5 (1S,4R)-6-((S)-Toluene-4-sulfinyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-diol 
• 187592-91-2 (1R,4S,4aS,5R,8S,9aR)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone 
• 187592-89-8 (1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone 
• 187592-94-5 (1R,4S,4aS,5R,8S,8aR,9aR,10aS)-4a-p-Tolylsulfanyl-1,4,4a,5,8,8a,9a,10a-octahydro-1,4;5,8-dimethano-anthraquinone 
• 187592-93-4 (1R,4S,4aS,5R,8S,9aR)-4a-p-Tolylsulfanyl-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone 
• 176706-59-5 (1R,4S,4aR,5R,8S,8aR,9aS,10aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,8a,9a,10a-octahydro-1,4;5,8-dimethano-anthraquinone 
• 161953-70-4 (5S,8R,SS)-5,8-methano-2-p-tolylsulfinyl-5,8-dihydro-1,4-naphthoquinone 

Relevant 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

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.

Influence of the sulfinyl group on the chemoselectivity and π-facial selectivity of diels-alder reactions of (S)-2-(p Tolylsulfinyl)-1,4-benzoquinone

Diels-Alder reactions of (S)-2-(p-tolylsulfmyl)-1,4-benzoquinone (1a) with cyclic (cyclopentadiene and cyelohexadiene) and acyclic dienes (1-[(trimethylsilyl)oxy]-1,3-butadiene and trans-piperylene) under different thermal and Lewis acid conditions are reported. Chemoselectivity (reactions on C2-C3 versus C5-C6 double bonds) is mainly related to the cyclic (on C5-C6) or acyclic (on C2-C3) structure of the diene. The high π-facial selectivity observed could be controlled by choosing adequate experimental conditions.

SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTIONS OF (S)-2-p-TOLYLSULFINYL-1,4-BENZOQUINONE

Optically pure (S)-2-p-tolylsulfinyl-1,4-benzoquinone (5) is readily obtained by deketalization of the corresponding quinone bisketal 4, synthesized by Andersen's type synthesis on 2-bromo-1,4-dimethoxybenzene (1) followed by anodic oxidation of the resulting sulfoxide.The Diels-Alder reaction of cyclopentadiene with 5 took place on C5-C6 dienophilic double bond showing high facial selectivity, which can be inverted by using different Lewis acids, and total endo selectivity.