75073-98-2

Upstream product

• 66684-74-0 dimethyl (E)-cinnamylidenemalonate 
• 1774-47-6 trimethylsulfoxonium iodide 
• 100-42-5 styrene 
• 17447-60-8 dimethyl 2-vinylcyclopropane-1,1-dicarboxylate 
• 14371-10-9 (E)-3-phenylpropenal 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 497179-36-9 dimethyl 2-[(9-benzyl-4,9-dihydro-1H-carbazol-1-yl)methyl]malonate 
• 1130593-94-0 (2R,5R)-dimethyl 2-(4-methoxyphenyl)-5-styryltetrahydrofuran-3,3-dicarboxylate 
• 1093350-41-4 dimethyl 2-(2-phenylethyl)cyclopropane-1,1-dicarboxylate 
• 1235889-80-1 (2S,5R)-dimethyl 1-(2-methoxybenzyl)-5-styryl-2-(thiophen-2-yl)pyrrolidine-3,3-dicarboxylate 
• 1235889-77-6 (2R,5R)-dimethyl 1-(2-methoxybenzyl)-2-phenyl-5-styrylpyrrolidine-3,3-dicarboxylate 

Relevant academic research and scientific papers

Palladium-Catalyzed Allylic Alkylation of Aldimine Esters with Vinyl-Cyclopropanes to Yield α,α-Disubstituted α-Amino Acid Derivatives

A synthetically useful approach for the synthesis of functionalized α, α-disubstituted α-amino acid derivatives via palladium-catalyzed 1,7 addition of readily available aldimine esters to vinylcyclopropanes is reported. This methodology was operated under mild conditions, affording α-allylic α-amino esters in good to excellent yields and excellent regio- and stereoselectivity. This transformation displays broad functional-group tolerance and enantioselective allylic alkylation has also been realized using a chiral phosphine ligand to provide the desired product. (Figure presented.).

An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters

A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.

Tetrahydro-1,3-oxazepines via Intramolecular Amination of Cyclopropylmethyl Cation

An efficient synthesis of tetrahydro-1,3-oxazepines was developed involving the regioselective intramolecular amination of cyclopropylmethyl cation. The cation was generated by the abstraction of one imidate group in bis-imidate bearing a carbocation-stabilizing substituent. Using 1,1,2,3-tetrasubstituted cyclopropane substrates, highly diastereoselective intramolecular amination to trans-tetrahydro-1,3-oxazepines was achieved. The resulting tetrahydro-1,3-oxazepines were transformed to the homoallylamine derivatives in high yields.

A route to highly functionalized-enaminoesters via a domino ring-opening cyclization/decarboxylative tautomerization sequence of donor-acceptor cyclopropanes with substituted malononitriles

An unprecedented and domino synthetic strategy for the synthesis of highly functionalized carbocyclic-enaminoesters bearing an all-carbon quaternary center via Yb(OTf)3-catalyzed ring-opening cyclization/decarboxylative tautomerization of donor-acceptor cyclopropanes with 2-alkyl malononitriles in excellent yields is described. The products are obtained as a single diastereomer in most cases where the nitrile and aryl groups are aligning in a cis orientation across the ring.

Diastereoselective synthesis of functionalized tetrahydrocarbazoles via a domino-ring opening-cyclization of donor-acceptor cyclopropanes with substituted 2-vinylindoles

A new domino synthetic approach for the synthesis of highly functionalized tetrahydrocarbazoles via DROC of various functionalized DA-cyclopropanes with 2-indolylnitroethylene and indole-substituted alkylidene malonate is described. The tetrahydrocarbazol

Advancing the reactivity of dimethylcyclopropane-1,1-dicarboxylates via cross metathesis

Cross metathesis of the readily available dimethyl 2-vinylcycloropane-1,1- dicarboxylate with a variety of olefins gave divergent access to new donor-acceptor cyclopropanes bearing a π-donor alkenyl substituent. The synthetic utility of these cyclopropanes was shown by their participation in cycloaddition reactions with nitrones to yield the anticipated tetrahydro-1,2-oxazines. Hydrogenation yielded the alkyl-substituted adducts which would be more difficult to access via other means. Georg Thieme Verlag Stuttgart New York.

A Novel Preparation of Electrophilic Cyclopropanes

Electrophilic cyclopropanes are conveniently prepared by decomposition of the corresponding Δ1-pyrazolines in the presence of a small amount of Ce(NH4)2(NO3)6.