37755-22-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 131, 1985 DOI: 10.1016/S0040-4039(00)61861-0

InChI:InChI=1/C14H14O4/c1-17-13(15)12(14(16)18-2)10-6-9-11-7-4-3-5-8-11/h3-10H,1-2H3/b9-6+

Upstream product

• 67-56-1 methanol 
• 676551-01-2 2-((Z)-3-Phenyl-allylidene)-malonic acid 
• 6773-29-1 dimethyl diazomalonate 
• 104-55-2 3-phenyl-propenal 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 500555-16-8 (2,3-dibromo-3-phenyl-propylidene)-malonic acid dimethyl ester 
• 352676-35-8 C₁₅H₁₆O₄ 
• 126301-15-3 (2R,3R,4R)-5-Oxo-3-((E)-styryl)-pyrrolidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester 
• 126301-11-9 (2S,3S)-2-Methoxycarbonyl-3-((E)-styryl)-4-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester 
• 1424279-44-6 dimethyl 3-phenyl-1-phthalimido-2,3-dihydro-1H-pyrrole-2,2-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.

Copper-catalyzed regiodivergent 1,4-and 1,6-conjugate silyl addition to diendioates: Access to functionalized allylsilanes

A copper-catalyzed regioselective 1,4-and 1,6-conjugate addition of a silyl reagent to diendioates was established. Various 1,4-and 1,6-protosilylation products were obtained in good yields and with high regioselectivity via tuning the ligands used in the reactions. This protocol has provided a simple and efficient method for the synthesis of multisubstituted functionalized allylsilanes.

Palladium-Catalyzed Asymmetric 1,6-Addition of Diarylphosphines to Allylidenemalonates for Chiral Phosphine Synthesis

A pincer-palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to allylidenemalonates has been developed for the synthesis of chiral allylic phosphines with up to 89% ee under mild conditions.

Lipase-catalyzed Knoevenagel condensation between α,β- unsaturated aldehydes and active methylene compounds

A simple and efficient Knoevenagel condensation between α,β-unsaturated aldehydes and active methylene compounds is reported. Notably, this condensation can be catalyzed by PPL (lipase from porcine pancreas) with satisfied yields (49%-92%). Moreover, PPL induces moderate Z/E selectivity in the Knoevenagel condensation.

A novel olefination of diazo-compounds with carbonyl compounds mediated by tributylstibine and catalytic amount of Cu(I)I

A one-pot reaction of tributylstibine, diazo-compounds including dimethyl diazomalonate, ethyl diazoacetate and diazoacetylacetone, carbonyl compounds and catalytic amount of Cu(I)I resulted in olefination in high yields.