205251-17-8

Upstream product

• 5804-85-3 diethylaluminium cyanide 
• 99930-83-3 (+)-(R)_S-ethynyl-p-tolylsulfoxide 
• 99930-83-3 (R)-ethynyl-p-tolyl-sulfoxide 
• 98147-48-9 2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate 

Downstream Products

• 314777-40-7 (1S*,2R*,6S*)-2-methyl-6-[(R)-p-tolylsulfinyl]-3-cyclohexene-1-carbonitrile 
• 314777-38-3 (1R,2R,6S)-2-methoxy-6-[(R)-(p-tolyl)sulfinyl]-3-cyclohexene-1-carbonitrile 
• 36650-74-5 pyrazolecarbonitrile 
• 1072909-08-0 ethyl 4-cyano-1-[4-hydroxy-1-methyl-2-[(4-methylphenyl)-disulfanyl]but-1-en-1-yl]-1H-pyrrole-2-carboxylate 
• 1072909-11-5 ethyl [5S,6R,7S,7aS,S(R)]-2-[2-(acetyloxy)ethyl]-7-cyano-3-methyl-6-(p-tolylsulfinyl)-5,6,7,7a-tetrahydropyrrolo[2,1-b][1,3]thiazole-5-carboxylate 
• 1283761-10-3 C₂₃H₂₂N₂O₃S 
• 1283760-97-3 C₂₃H₂₂N₂O₃S 
• 128353-03-7 Ethyl 1-cyanopyrrolo<5,1-a>isoquinoline-3-carboxylate 
• 38693-82-2 5-methyl-1H-pyrazole-3-carbonitrile 
• 34726-95-9 β-sulfenylacrylamide 

Relevant academic research and scientific papers

(Z)-3-p-tolylsulfinylacrylonitriles as chiral dipolarophiles: Reactions with diazoalkanes

(figure presented) The dipolarophilic reactivity of enantiopure (Z)-3-p-tolylsulfinylacrylonitriles (1) has been evaluated with diazoalkanes. 3-Cyanopyrazoles are obtained when R = H, but with R = alkyl (Bn, n-Bu, and t-Bu) only one cycloadduct (4 or 5) is formed in high yield under mild conditions, therefore evidencing a complete control of the regioselectivity and the endolexo and π-facial selectivities. These reactions are a new straightforward entry to the synthesis of pyrazolines and related structures and reveal the excellent dipolarophilic features of (Z)-sulfinylacrylonitriles.

Synthesis and Dienophilic Behavior of Enantiomerically Pure (Z)-3-p-Tolylsulfinylacrylonitriles

The syntheses of enantiomerically pure (Z)-3-p-tolylsulfinylacrylonitrile (1b) and its 2-n-butyl (1a), 2-tert-butyl (1c), and 2-benzyl (1d) derivatives, by stereoselective hydrocyanation with Et2AlCN of their corresponding alkynylsulfoxides, are described. Asymmetric Diels-Alder reactions of these dienophiles with cyclopentadiene are also reported, the most significant finding being their total π-facial diastereoselectivity, controlled by the sulfur configuration, which can be readily inverted by using BF3 as a catalyst. The endo selectivity is very high for 1b under thermal and catalytic (ZnBr2) conditions and complete in the presence of BF3, whereas 1a and 1d only exhibit a complete endo selectivity in the presence of BF3.