1110700-53-2

Upstream product

• 6773-29-1 dimethyl diazomalonate 
• 612-15-7 o-methoxystyrene 
• 868-26-8 dimethyl 2-bromomalonate 
• 22621-54-1 2-Methoxy phenyl methylene-propanedioic acid dimethyl ester 
• 1774-47-6 trimethylsulfoxonium iodide 
• 108-59-8 malonic acid dimethyl ester 
• 135-02-4 ortho-anisaldehyde 

Downstream Products

• 1577201-80-9 dimethyl 2-((N,4-dimethylphenyl)sulfonamido)-3-pentyl-4-(o-methoxyphenyl)cyclopent-2-ene-1,1-dicarboxylate 

Relevant academic research and scientific papers

Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate

We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: a) a regenerable solvent, b) a Br?nsted acid inducing diverse transformations via general acid catalysis, and c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, respectively, in a single time-efficient step. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations.

Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones

An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained Csp3?Csp3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.

Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans

Donor–acceptor cyclopropanes were engaged in a [3+3]-annulation reaction with γ-hydroxyenones. Sc(OTf)3was found to be the best catalyst, and 2,4,4,5-tetrasubstituted tetrahydropyran products were obtained in good yields under mild reaction con

A facile formal [2+1] cycloaddition of styrenes with alpha-bromocarbonyls catalyzed by copper: Efficient synthesis of donor-acceptor cyclopropanes

Reactions of 2-bromoesters and styrenes underwent a [2+1] cycloaddition reaction, i.e., cyclopropanation, to produce donor-acceptor (D-A) cyclopropanes through a radical addition-ring closure process. In this reaction, the combination of copper(ii) comple

Catalysis and chemodivergence in the interrupted, formal homo-nazarov cyclization using allylsilanes

A chemodivergent, Lewis acid catalyzed allylsilane interrupted formal homo-Nazarov cyclization is disclosed. With catalytic amounts of SnCl4 and in the presence of allyltrimethylsilane, a formal Hosomi-Sakurai-type allylation of the oxyallyl cation intermediate is observed. A variety of functionalized donor-acceptor cyclopropanes and allylsilanes were shown to be amenable to the reaction transformation and the allyl products were formed in up to 92% yield. Under dilute reaction conditions with stoichiometric SnCl4 and at reduced temperatures, an unusual formal [3 + 2]-cycloaddition between the allylsilane and the oxyallyl cation occurred to give hexahydrobenzofuran products in up to 69% yield.

TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides: Synthesis of highly functionalized triazinines and azetidines

A TiCl4 promoted formal [3 + 3] cycloaddition of cyclopropane 1,1-diesters with azides has been developed for the synthesis of highly functionalized triazinines. Both stoichiometric and substoichiometric versions of this reaction were accomplished dependent on the choice of solvent. It is noteworthy that the corresponding products could be easily converted to biologically important azetidines by simple thermolysis.

Rhodium-catalyzed cyclopropanation of alkenes with dimethyl diazomalonate

The outstanding ability of dirhodium α,α,α′, α′-tetramethyl-1,3-benzenedipropanoate [Rh2(esp) 2; esp=α,α,α′,α′-tetramethyl-1,3- benzene-dipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate-derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.