127604-91-5

Upstream product

• 38323-22-7 dimethyl (4-nitrobenzylidene)malonate 
• 100-13-0 4-nitrostyrene 
• 145838-86-4 bis(methoxycarbonyl)(phenyliodinio)methanide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 555-16-8 4-nitrobenzaldehdye 
• 108-59-8 malonic acid dimethyl ester 
• 6773-29-1 dimethyl diazomalonate 
• 186581-53-3 diazomethane 
• 127604-87-9 (7S,10R)-7-Isopropyl-10-methyl-3-(4-nitro-benzylidene)-1,5-dioxa-spiro[5.5]undecane-2,4-dione 
• 127604-89-1 (1S,7S,10R)-7-Isopropyl-10-methyl-1-(4-nitro-phenyl)-5,12-dioxa-dispiro[2.2.5.2]tridecane-4,13-dione 

Relevant academic research and scientific papers

Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

A method has been developed for the synthesis of substituted β-styrylmalonates by conversion of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) in the presence of gallium trichloride into the corresponding- 1,2-zwitterionic intermediates or (2-arylethyl-idene)malonates, followed by treatment with pyridine at room temperature leading to an isomerization of the emerging double bond. This method allows one to expand these reactions to include ACDCs with acceptor substituents at the aromatic ring.

(3+2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiocyanate: A Facile and Efficient Synthesis of 2-Amino-4,5-dihydrothiophenes

An easy and efficient route to obtain 2-amino-4,5-dihydrothiophenes is presented. A formal (3+2)-cycloaddition of donor-acceptor cyclopropanes and ammonium thiocyanate catalyzed by Yb(OTf) 3delivers the desired products in good to excellent yields. A broad range of functional groups is tolerated during this process.

(3 + 2)-Cycloaddition of Donor-Acceptor Cyclopropanes with Selenocyanate: Synthesis of Dihydroselenophenes and Selenophenes

We present a Lewis-acid-catalyzed (3 + 2)-cycloaddition of donor-acceptor cyclopropanes and selenocyanate (as its tetramethylammonium salt) for the synthesis of dihydroselenophenes. The transformation proceeded with moderate to excellent yields and showed a high functional group tolerance. Further oxidation using DDQ delivered selenophenes.

Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis

Donor-acceptor cyclopropanes were reacted under Lewis acid catalysis with 3-thioxocyclobutanones as surrogates for disubstituted thioketenes. A broad scope of 2-substituted tetrahydrothiophenes with a semicyclic double bond was obtained under mild conditions with high functional group tolerance and in excellent yield. A sequence of a formal [3 + 2]-cycloaddition followed by the subsequent release of disubstituted ketene is postulated as the mechanism.

Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes Catalyzed by a Br?nsted Acid in Hexafluoroisopropanol

A general, Br?nsted acid catalyzed method for the room temperature, nucleophilic ring opening of donor-acceptor cyclopropanes in fluorinated alcohol solvent, HFIP, is described. Salient features of this method include an expanded cyclopropane scope, including those bearing single keto-acceptor groups and those bearing electron-deficient aryl groups. Notably, the catalytic system proved amenable to a wide range of nucleophiles including arenes, indoles, azides, diketones, and alcohols.

Scandium(III) Trifluoromethanesulfonate Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 1,1-Diphenylethanols: An Approach to Polysubstituted Olefins

An unexpected synthetic approach to polysubstituted olefins through the scandium(III) trifluoromethanesulfonate catalyzed ring-opening reaction of donor–acceptor cyclopropanes with 1,1-diphenylethanols was developed. The reactions, which are experimentally easy to handle, feature tolerance of various functional groups and mild reaction conditions. On the basis of experimental evidence, a plausible mechanism was also proposed.

Stereoselective double lewis acid/organo-catalyzed dimerization of donor-acceptor cyclopropanes into substituted 2-oxabicyclo[3.3.0]octanes

A new approach for the dimerization of donor-acceptor cyclopropanes (2-arylcyclopropane-1,1-dicarboxylates) under double-catalysis conditions by treatment with 20 mol % of GaCl3 and dimethyl 3,5-dimethyl-1- pyrazoline-3,5-dicarboxylate as a specific organocatalyst has been found. Under these conditions, the starting compounds are regio- and stereospecifically converted into polysubstituted 2-oxabicyclo[3.3.0]octanes. Two new rings, one C-O bond, and two C-C bonds are formed in this process, and four stereocenters are thus created. The reaction mechanism was thoroughly studied by NMR spectroscopy, and a number of intermediates were detected.

Cycloadditions of aromatic azomethine imines with 1,1-cyclopropane Diesters

The cycloaddition of aromatic azomethine imines to 1,1-cyclopropane diesters was achieved using Ni(CIO4)2 as catalyst. The methodology gives access to unique tricyclic dihydroquinoline derivatives with dr up to 6.6:1. A nonconcerted

CYCLOADDITIONS IN SYNTHESES.PART 41. CHIRAL SPIROCYCLIC 5-ARYL-METHYLENE-1,3-DIOXANE-4,6-DIONES AS NOVEL SYNTHONS FOR ENANTIOMERICALLY PURE 2-ARYLCYCLOPROPANE-1,1-DICARBOXYLATES

E- and Z- isomers of spirocyclic 5-arylmethylene-1,3-dioxane-4,6-dione, useful synthons for enantiomerically pure cyclopropane-1,1-dicarboxylates, have been synthesized from 1-menthone.Their diastereofacial selectivity is explained by a boat conformation in their dioxanedione ring.

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.