100747-48-6

Upstream product

• 591-50-4 iodobenzene 
• 100747-44-2 dimethyl 2,3-butadienylmalonate 
• 51608-60-7 phenyl N-tosyl imine 
• 3360-54-1 3-bromo-2-phenylprop-1-ene 
• 1392283-24-7 C₁₇H₂₀O₄ 
• 108-59-8 malonic acid dimethyl ester 
• 4469-66-3 4-Phenyl-2-methoxycarbonyl-4-enoic acid methyl ester 

Downstream Products

• 115340-08-4 dimethyl 3-phenylcyclopentane-1,1-dicarboxylate 

Relevant academic research and scientific papers

FeCl3-Catalyzed Ring-Closing Carbonyl–Olefin Metathesis

Exploiting catalytic carbonyl–olefin metathesis is an ongoing challenge in organic synthesis. Reported herein is an FeCl3-catalyzed ring-closing carbonyl–olefin metathesis. The protocol allows access to a range of carbo-/heterocyclic alkenes wi

Reverse of regioselectivity in intramolecular nucleophilic substitution of π-allyl palladium species. Highly selective formation of vinylic cyclopropanes via the pd(0)-catalyzed coupling-cyclization reaction of organic iodides with 2-(2′,3′-dienyl)malonates

(formula presented) Vinylic cyclopropanes were formed highly selectively via the Pd(PPh3)4-catalyzed insertion-intramolecular nucleophilic substitution reaction of aryl or 1-alkenyl iodides with 2-(2′,3′-dienyl)malonates. The regioselectivity observed here is different from what was reported by Cazes et al.

Pd0-catalyzed three-component tandem double-addition-cyclization reaction: Stereoselective synthesis of cis-pyrrolidine derivatives

Cis-2,5-Disubstituted pyrrolidine skeletons have been constructed by the Pd0- catalyzed three-component tandem double-addition-cyclization reaction of 2-(2,3-butadienyl)malonates, organohalides, and imines (see scheme, yields: 81-100%; cis/tran

Chiral hetero- and carbocyclic compounds from the asymmetric hydrogenation of cyclic alkenes

Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates. Copyright

Control of regioselectivity in Pd(0)-catalyzed coupling-cyclization reaction of 2-(2′,3′-allenyl)malonates with organic halides

The regioselectivity in the Pd(0)-catalyzed coupling-cyclization of 2-(2′,3′-allenyl)malonates with organic halides is determined by the steric and electronic effects of both substrates. By deliberate control of the reaction conditions, the regioselectivity of this reaction can be tuned. With conditions A and B, the reaction afforded vinylic cyclopropane derivatives, while with conditions C and D, the reaction afforded cyclopentene derivatives in a highly selective manner. Under similar conditions, 1-alkenyl halides tend to form more three-membered cyclic products. The increased steric hindrance at the 2′-positon of the allene moiety and aryl halides favors the formation of five-membered cyclic products. The regioselectivity of the reaction may be explained by the comparison of the relative stabilities of syn- and anti-type π-allyl palladium intermediates.

Carbopalladation of Β-allenylmalonates: a way to cyclopentenyl or vinylcyclopropyl derivatives.

The palladium-catalyzed addition of a vinyl or aryl halide to the enolate of Β-allenyl malonate 2 leads to the formation of either of the two cyclized products 3 and 4 depending mainly on the bulk of the starting unsaturated halide.