65715-04-0

Upstream product

• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 112068-21-0 rac-(E)-2-hydroxy-4-phenyl-3-butenoic acid methyl ester 
• 140653-89-0 (E)-benzylideneglyoxylic acid potassium salt 
• 100-52-7 benzaldehyde 
• 107969-78-8 methyl benzylidenepyruvate 

Downstream Products

• 104132-62-9 (E)-N-(2-Oxo-4-phenyl-3-butenoyl)-1-pyrrolidincarboximidoylchlorid 
• 104132-64-1 (E)-N-(2-Oxo-4-phenyl-3-butenoyl)-4-morpholincarboximidoylchlorid 
• 104132-60-7 (E)-Dimethylamino-N-(2-oxo-4-phenyl-3-butenoyl)formimidoylchlorid 
• 288589-97-9 4-hydroxy-4-phenyl-but-2-enoic acid 
• 1346260-92-1 2-hydroxy-4-phenylbut-3-enoic acid 2-isopropyl-5-methylcyclohexyl ester 
• 129029-61-4 2-hydroxy-4-phenylbut-3-enoic acid 

Relevant academic research and scientific papers

Tandem hetero Diels-Alder reaction: Synthesis of oxygenated macrocycles

Equation presented C2-symmetric oxygenated macrocycles have been synthesized from simple acyclic precursors in a single step by a tandem hetero Diels-Alder reaction. Thermolysis and Lewis acid catalysis can effect this novel transformation. The tandem rea

Synthesis of chiral bispirotetrahydrofuran oxindoles by cooperative bimetallic-catalyzed asymmetric cascade reaction

A new, efficient route for the enantioselective construction of bispirotetrahydrofuran oxindoles is described via the cooperative dinuclear zinc-AzePhenol catalyst. Under mild conditions, a broad range of bispirotetrahydrofuran oxindoles have been synthesized with excellent stereoselectivities through the cascade Michael/hemiketalization/Friedel-Crafts reaction of β,γ-unsaturated α-ketoamide and 2-hydroxy-1-indanone. The reaction can be performed on a gram scale with low catalyst loading (2 mol %) without impacting its efficiency.

Access to Chiral 2,5-Pyrrolidinyl Dispirooxindoles via Dinuclear Zinc-Catalyzed Asymmetric Cascade Reactions

A series of new nonsymmetric semi-azacrown ether ligands were developed and applied to the asymmetric Michael/cyclic keto-imine formation/Friedel-Crafts alkylation reactions of 3-amino oxindole hydrochlorides and β,γ-unsaturated α-keto amides. A diversity of 2,5-pyrrolidinyl dispirooxindoles containing two nonadjacent spiro-quaternary stereocenters were obtained in excellent diastereoselectivities and moderate to excellent enantioselectivities (up to 95% ee). A possible catalytic cycle was proposed to explain the origin of the asymmetric induction.

Catalyst-controlled diastereoselectivity reversal in the formation of dihydropyrans

An enantioselective synthesis of cis-dihydropyrans as the formal HDA reaction products was achieved through the catalyst-controlled anti-selective conjugate addition of aldehydes to β,γ-unsaturated α-keto esters. The observed unusual cis-selectivity could

N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones

The umpolung of alkynyl 1,2-diketones via N-heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important α-pyrones under very mild conditions. A completely new NHC-catalyzed umpolung pattern involving an O-acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway, featured by a series of group migrations and new bond formation, was postulated to demonstrate the formation of the products. (Figure presented.).

Tandem N -alkylation/vinylogous aldol reaction of β,γ-Alkenyl α-iminoester

This report describes a highly regioselective tandem N-alkylation/ vinylogous aldol reaction of β,γ-alkenyl α-iminoesters. The sulfur group improves the regioselectivity of the directed vinylogous aldol reaction, providing a new synthetic method of 3-amino-2-pyrones.

Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes

The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.

Structure and absolute configuration of new acidic metabolites from Stachys ehrenbergii

Two novel metabolites have been isolated from the aerial parts of Stachys ehrenberiigii. Their structures and stereochemistry were elucidated using a combination of 13C and 1H homo and heteronuclear 2D NMR experiments and mass analysis. The development of an enantioselective synthesis of 3-(2′-acetoxy-4-phenylbut-3′-enoylamino)propionic acid allowed to confirm the structure and assign the (R) absolute configuration at C-2′ of the natural product.

Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride

Breaking the bottleneck: α-Keto carboxylic acids and N-heterocyclic carboxylic acids are activated in situ with oxalyl chloride then catalytically alkynylated to give ynediones and N-heterocyclic ynones efficiently in a one-pot fashion. 5-Acylpyrazoles and 2-phenylaminopyrimidines, potentially interesting for pharmaceutical applications, are readily synthesized in concise one-pot, three-component syntheses. Copyright

Asymmetrie aerobic oxidation of α-hydroxy acid derivatives by C 4-symmetric, vanadate-centered, tetrakisvanadyl(V) clusters derived from N-salicylidene-α-aminocarboxylates

(Chemical Equation Presented) A series of chiral vanadyl(V) methoxides bearing 3-t-butyl-5-substituted N-salicylene-L-valinate and L-t-leucinate as chiral auxiliaries has been prepared. In all cases except the 3,5-di-t-butyl analogue, they exist as monomers both in solution and in the single crystal state. In the case of the 3,5-di-t-butyl analogue, the architectural nature of the vanadyl(V) complex highly depends on the base used during the complex formation event. A pentanuclear C4-symmetric complex was formed when potassium salts were employed instead of the corresponding sodium salts. A central vanadate(V) unit serves to grip four identical chiral monomelic vanadyl(V) units together, by which a potassium ion sits on top of the four flanking units through carbonyl coordinations and serves to hold the whole cluster by cooperation with the central vanadate(V) unit. In comparison with the corresponding monomelic vanadyl(V) methoxide complex, the cluster complex was utilized to facilitate the asymmetric aerobic oxidations of various racemic α-hydroxyesters, -amides, and -thioesters with excellent selectivity factors (krel 40 to >500).