77588-51-3

Upstream product

• 98-01-1 furfural 
• 583-06-2 3-benzoylacrylic acid 
• 117937-07-2 4-Furan-2-yl-4-hydroxy-1-phenyl-but-2-yn-1-one 
• 17851-99-9 1-phenyl-2-tributylstannyl-1-ethanone 
• 111886-29-4 tert-butyldimethyl((1-(furan-2-yl)vinyl)oxy)silane 
• 40126-68-9 (E)-4-Furan-2-yl-4-oxo-but-2-enoic acid 
• 100-52-7 benzaldehyde 
• 1777-60-2 [(furan-2-ylcarbonyl)methylene]triphenylphosphorane 
• 163667-14-9 2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 148204-86-8 (tert-butyldimethylsilanyloxy)phenylacetic acid methyl ester 
• 4358-87-6 (RS)-methyl mandelate 
• 611-71-2 MANDELIC ACID 
• 532-27-4 1-chloroacetophenone 
• 66929-53-1 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione 

Relevant academic research and scientific papers

Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei

A method of synthesizing chiral alkene propyl alcohol

The invention discloses a method for synthesizing chiral alkene propyl alcohol method, which belongs to the technical field of organic chemistry. The method adopts the [...] derived binaphthol potassium salt as a chiral [...] catalyst, catalytic [...] pro

Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies

The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Br?nsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure-enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Br?nsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Br?nsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.

Mild Homologation of Esters through Continuous Flow Chloroacetate Claisen Reactions

The selective chloromethylenation of functionalized esters using chloroacetic acid (CA) and LiHMDS (HMDS=hexamethyldisilazide) in a continuous-flow setup is reported. This Claisen homologation is for the first time extended to bis-chloromethylenation using dichloroacetic acid (DCA), thus giving access to under-explored α,α′-bis-chloroketones. The use of flow conditions enables efficient generation and reaction of the unstable chloroacetate dianion intermediates, leading to unprecedented mild and scalable reaction conditions at an economical reagent stoichiometry (?10 °C, 1 min, 1.0–2.4 equiv dianion). The clean reaction profiles allow subsequent use of the unpurified crude products, which is demonstrated in the synthesis of various heterocycles of broad interest. Furthermore, we report a novel, catalyst-free substitution of the obtained monochloro ketone products with (hetero)aryl zinc enolates to give valuable 1,4-diketones.

Detrifluoroacetylation Reaction of Trifluoromethyl-β-diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4-Diketones

Currently, a great deal of research efforts are focused on C–C bond activation for development of novel synthetic methodology. In this paper, a detrifluoroacetylation of trifluoromethyl-β-diketones is described, which allows for the synthesis of succinimides and 1,4-diketones through cascade Michael addition/retro-Claisen reaction and nucleophilic substitution/retro-Claisen reaction. The readily available trifluoromethyl-β-diketones, wide substrate scope, and mild conditions make this method very practical.

Stereospecific construction of chiral tertiary and quaternary carbon by nucleophilic cyclopropanation with bis(iodozincio)methane

The reaction of a ketone having a leaving group at the aposition, such as a,bepoxy ketone or asulfonyloxy ketone, with bis(iodozincio) methane affords a zinc alkoxide of cyclopropanol. The reaction proceeds by nucleophilic addition of the dizinc to the carbonyl group and a sequential intramolecular nucleophilic substitution of the introduced iodozinciomethyl group to the adjacent electrophilic carbon that has a leaving group. When an optically active a,β-epoxy ketone or asulfonyloxy ketone is treated with the dizinc, a zinc alkoxide of cyclopropanol having a chiral tertiary or quaternary carbon in the cyclopropane ring is obtained, and the obtained zinc alkoxide of cyclopropanol acts as a chiral ho-moenolate. When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active a-tertiary or -quaternary ketone that retains high optical purity.

Preparation of zinc-homoenolate from α-sulfonyloxy ketone and bis(iodozincio)methane

Treatment of α-sulfonyloxy ketone with bis(iodozincio)-methane gives a zinc cyclopropoxide which is formed via a nucleophilic addition of the reagent to carbonyl group followed by an intramolecular substitution reaction. Copyright

Oxidative Generation of α-Radicals of Carbonyl Compounds from the α-Stannyl Derivatives and Their Reactions with Electron-Rich Olefins

The oxidation of α-tributylstannyl alkanoates with tetrabutylammonium hexanitratocerate(IV) generates α-radicals of the alkanoates by eliminating the stannylium ion.The thus-formed radicals react with various electron-rich olefinic compounds, such as silyl enol ethers, giving addition products in good yield.This method formally achieves selective cross coupling between alkanoates and ketones.

THE REACTION OF ALKYL 4-HYDROXY-2-ALKYNOATES AND 4-HYDROXY-2-ALKYN-1-ONES WITH PALLADIUM TRIBUTYLAMMONIUM FORMATE AND WITH TRIBUTYLAMINE: PREPARATION OF 1,4-DICARBONYL COMPOUNDS

Ethyl 4-oxo-2-alkenoates and 1,4-dioxo-2-alkenes are easily prepared by treating ethyl 4-hydroxy-2-alkynoates and 4-hydroxy-2-alkyn-1-ones with n-tributylamine.Treatment of ethyl 4-hydroxy-2-alkynoates and 4-hydroxy-2-alkyn-1-ones with palladium-tributylammonium formate produces ethyl 4-oxo-alkanoates and 1,4-alkandiones in good to high yield through a novel one-pot isomerization/hydrogenation reaction.

Addition of Aldehydes to Activated Double Bonds, XXV. Syntheses and Reactions of Branched Tricarbonyl Compounds

Thiazolium salt-catalyzed addition of aldehydes to arylidene- and alkylidene-β-dicarbonyl compounds as well as to 3-acylacrylic esters leads to branched tricarbonyl compounds (1 - 26), which are useful reagents for the synthesis of heterocyclic compounds.