58769-52-1

Upstream product

• 100-52-7 benzaldehyde 
• 101-41-7 benzeneacetic acid methyl ester 
• 7476-66-6 methyl 2-chloro-2-phenylethanoate 
• 67-56-1 methanol 
• 4603-32-1 α-benzenessigsaeure 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 93434-58-3 methyl 3-hydroxy-2,3-diphenylpropionate 
• 4603-32-1 (2RS,3RS)-3-hydroxy-2,3-diphenyl-propionic acid 
• 54108-62-2 3-Oxo-2,3-diphenylpropenoic acid methyl ester 
• 22979-35-7 Methyl phenyldiazoacetate 
• 53172-91-1 (benzyloxy)(tert-butyl)dimethylsilane 
• 1431563-88-0 (2S,3S)-methyl 3-((tert-butyldimethylsilyl)oxy)-2,3-diphenylpropanoate 
• 421-20-5 Methyl fluorosulfonate 
• 186581-53-3 diazomethane 

Downstream Products

• 369386-17-4 (2S,3S)-methyl 2-phenyl-2,3-dihydrobenzofuran-3-carboxylate 
• 96923-93-2 C₁₇H₁₅N₃O 

Relevant academic research and scientific papers

Visible-Light-Driven, Metal-Free Divergent Difunctionalization of Alkenes Using Alkyl Formates

In recent decades, difunctionalization of alkenes has received considerable attention as an efficient and straightforward way to increase molecular complexity. However, examples of the difunctionalization of alkenes initiated by the intermolecular addition of alkoxycarbonyl radicals providing substituted alkanoates are still rare. Herein, we present the visible light-driven metal-free divergent difunctionalization of alkenes triggered by the intermolecular addition of alkoxycarbonyl radicals under ambient conditions. Employing alkyl formates as precursors of alkoxycarbonyl radicals and 4CzIPN as the photocatalyst, a variety of substituted alkanoates, including β-alkoxy, β-hydroxy, β-dimethoxymethoxy, and β-formyloxy alkanoates, could be facilely accessed with high functional group tolerance and high efficiency. Moreover, the mechanism study revealed that β-hydroxy alkanoates were generated by a selective decomposition of orthoformates promoted by the N-alkoxyazinium salt.

Phosphine Oxide Catalyzed, Tetrachlorosilane-Mediated Enantioselective Direct Aldol Reactions of Thioesters

The stereoselective direct aldol reaction of S-phenyl thioesters and aromatic aldehydes promoted by tetrachlorosilane was realized for the first time; the proposed mechanism involves the formation of a chiral cationic hypervalent silicon species and requi

Overriding effect of temperature over reagent and substrate size for boron-mediated aldol reaction of methyl phenylacetate

The enolization temperature overrides all other aspects, including the sterics of the alkyl group of the boron reagent and the alkoxy group of the ester during the enolboration-aldolization of phenylacetates. This study has led to the first n-Bu2/su

Sequential C-H functionalization reactions for the enantioselective synthesis of highly functionalized 2,3-dihydrobenzofurans

The enantioselective synthesis of 2,3-dihydrobenzofurans was achieved by using two sequential C-H functionalization reactions, a rhodium-catalyzed enantioselective intermolecular C-H insertion followed by a palladium-catalyzed C-H activation/C-O cyclization. Further diversification of the 2,3-dihydrobenzofuran structures was possible by a subsequent palladium-catalyzed intermolecular Heck-type sp2 C-H functionalization.

Discovery of a novel class of aldol-derived 1,2,3-triazoles: Potent and selective inhibitors of human cytochrome P450 19A1 (aromatase)

The discovery of a novel five-component 1,2,3-triazole-containing pharmacophore that exhibits potent and selective inhibition of aromatase (CYP 450 19A1) is described. All compounds are derived from an initial aldol reaction of a phenylacetate derivative

Solvent- or temperature-controlled diastereoselective aldol reaction of methyl phenylacetate

Unlike the enolboration-aldolization of methyl propanoate, the choice of either the solvent or temperature determines the diastereoselectivity during the enolboration-aldolization of methyl phenylacetate. In CH2Cl 2, the reaction favors the anti-pathway at -78 °C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.

Control of diastereoselectivity in the aldolization of methyl phenylacetate

The aldolization of methyl phenylacetate with benzaldehyde in several conditions was studied. While the use of LDA in THF-HMPA gave the anti-aldol, the dibutylboron triflate furnished the syn-aldol in high diastereoselectivity (syn:anti=97:3). (C) 2000 El

Diastereoselective reactions of 1,1′-bihaphthyl ester enolates with carbonyl electrophiles

Diastereoselectivity in the aldol and the conjugate additions of 2′-hydroxy-1,1′-binaphthyl ester enolates with a variety of carbonyl electrophiles has been examined. The ester enolate generated by BuLi reacts with several aldehydes to give the threo products preferentially with high diastereoselectivity and in good yield. Satisfactory diastereoselectivity has also been observed in the minor erythro derivatives. A mechanistic interpretation of the results is made on the basis of the absolute stereochemistry of the products.

The Phenyldimethylsilyl Group as a Masked Hydroxy Group

A phenyldimethylsilyl group attached to carbon can be converted into hydroxy group 1->5, with retention of configuration at the migrating carbon, by any of three main methods.The first involves protodesilylation, to remove the phenyl ring from the silicon atom, followed by oxidation of the resulting functionalized silicon atom using peracid or hydrogen peroxide.The second uses mercuric acetate for the same purpose, and can be combined in one pot with the oxidative step using peracetic acid.This method has a variant in which the mercuric ion is combined with palladium(II) acetate, both in less than stoichiometric amounts.The third uses bromine, which can also be used in one pot in conjuction with peracetic acid.In this method, but not in the method based on mercuric acetate, the peracetic acid may be buffered with sodium acetate.The method using bromine as the electrophile for removing the benzene ring has a more agreeable variant in which it is administered in the form of potassium bromide, which is oxidised to bromine by the peracetic acid.The scope and limitations of each of these methods are reported with a range of examples possessing between them many of the common functional groups.Simple benzene rings, alcohols, ethers, esters, amides and nitriles are compatible with all three methods, and ketones do not undergo Baeyer-Villiger reaction under any of the conditions.Amines, however, are oxidised to amine oxides.Ketones may be brominated in the third of the three main species.The absence of acid in the third method makes it especially valuable when the phenyldimethylsilyl group has a neighbouring nucleofugal group such as hydroxy or acetoxy.Carbon-carbon double bonds are incompatible with the methods, except for terminal monosubstituted double bonds, which can survive the conditions used in the first of the three methods.