40394-84-1

Upstream product

• 105-36-2 ethyl bromoacetate 
• 93-55-0 1-phenyl-propan-1-one 
• 115205-58-8 1-Phenyl-1-phenylsulfanyl-propan-2-ol 
• 35874-96-5 Phenyl(phenylthio)acetaldehyd 
• 10371-49-0 1-phenyl-1-(phenylthio)-2-propenone 
• 623-70-1 ethyl (E)-crotonate 
• 5908-41-8 benzoyltrimethylsilane 
• 594-02-5 1,1-diiodoethane 
• 557-20-0 diethylzinc 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 30085-70-2 4-(1-phenyl-propenyl)-morpholine 
• 623-73-4 diazoacetic acid ethyl ester 
• 331991-59-4 ethyl 3-methyl-4-(3,5-dimethylpyrazol-1-yl)-4-oxobutanoate 
• 115205-59-9 (E)-3-Methyl-4-phenyl-4-phenylsulfanyl-but-3-enoic acid ethyl ester 

Downstream Products

• 101073-95-4 ethyl 3-methyl-4-phenyl-4-butanoate 
• 26620-41-7 (RS,SR)-γ-hydroxy-β-methyl-γ-phenylbutanoic acid lactone 
• 26704-17-6 trans-3-methyl-4-phenylbutan-4-olide 

Relevant academic research and scientific papers

Efficient synthesis of γ-keto esters from enamines and EDA

The reaction of enamines with ethyl diazoacetate (EDA) catalyzed by dirhodium and copper complexes provided γ-keto esters in good yields. The influences of catalyst, reaction solvent, temperature, and structure of enamines on this transformation were inve

Copper-Catalyzed Synthesis of γ-Amino Acids Featuring Quaternary Stereocenters

The first general asymmetric synthesis of γ,γ-disubstituted γ-amino acids by copper-catalyzed ring opening of nonstrained lactones with amines is reported. This approach features ample scope, operational simplicity, and wide functional-group diversity. The catalytic process allows access to a series of highly functionalized enantioenriched γ-amino acids featuring quaternary stereocenters with excellent enantiomeric ratios of up to 98:2 and excellent yields of up to 98 %.

Photoredox-Catalyzed Hydroacylation of Olefins Employing Carboxylic Acids and Hydrosilanes

A hydroacylation reaction of alkenes has been achieved employing readily available carboxylic acids as the acyl source and hydrosilanes as a hydrogen source via photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps has dramatically expanded new applications of carboxylic acids in organic synthesis. The protocol also features extremely mild conditions, broad substrate scope, and good functional group tolerance, affording a novel and convenient approach to hydroacylation of alkenes.

Formation of β-substituted γ-keto esters via zinc carbenoid mediated chain extension

The conversion of β-keto esters into β-methylated γ-keto esters can be achieved through treatment with zinc carbenoids derived from 1,1-diiodoethane. The incorporation of a β-phenyl substituent is also possible through treatment with diiodotoluene. Georg

Metallophosphite-induced nucleophilic acylation of α,β- unsaturated amides: Facilitated catalysis by a diastereoselective retro [1,4] brook rearrangement

(Chemical Equation Presented) Intermolecular alkene acylation reactions between acyl silanes and α,β-unsaturated amides with metallophosphite catalysis afford α-silyl-γ-ketoamides with high diastereoselectivities (see scheme). These can be converted into

Carbon-carbon bond formation by radical addition-fragmentation reactions of O-alkylated enols

α-tert-Butoxystyrene [H2C = C(OBut)Ph] reacts with α-bromocarbonyl or α-bromosulfonyl compounds [R 1R2C(Br)EWG; EWG = -C(O)X or -S(O2)X] to bring about replacement of the bromine atom by the phenacyl group and give R 1R2C(EWG)CH2C(O)Ph. These reactions take place in refluxing benzene or cyclohexane with dilauroyl peroxide or azobis(isobutyronitrile) as initiator and proceed by a radical-chain mechanism that involves addition of the relatively electrophilic radical R 1R2(EWG)C* to the styrene. This is followed by β-scission of the derived α-tert-butoxybenzylic adduct radical to give But*, which then abstracts bromine from the organic halide to complete the chain. α-1-Adamantoxystyrene reacts similarly with R 1R2C(Br)EWG, at higher temperature in refluxing octane using dα-tert-amyl peroxide as initiator, and gives phenacylation products in generally higher yields than are obtained using α-tert-butoxystyrene. Simple iodoalkanes, which afford relatively nucleophilic alkyl radicals, can also be successfully phenacylated using α-1-adamantoxystyrene. O-Alkyl O-(tert-butyldimethylsilyl) ketene acetals H2C=C(OR)OTBS, in which R is a secondary or tertiary alkyl group, react in an analogous fashion with organic halides of the type R1R2C(Br)EWG to give the carboxymethylation products R1R2C(EWG)CH 2CO2Me, after conversion of the first-formed silyl ester to the corresponding methyl ester. The silyl ketene acetals also undergo radical-chain reactions with electron-poor alkenes to bring about alkylation-carboxymethylation of the latter. For example, phenyl vinyl sulfone reacts with H2C=C(OBut)OTBS to afford Bu tCH2CH(SO2Ph)CH2CO2Me via an initial silyl ester. In a more complex chain reaction, involving rapid ring opening of the cyclopropyldimethylcarbinyl radical, the ketene acetal H 2C=C(OCMe2C3H5-cyclo)OTBS reacts with two molecules of N-methyl- or N-phenyl-maleimide to bring about [3 + 2] annulation of one molecule of the maleimide, and then to link the bicyclic moiety thus formed to the second molecule of the maleimide via an alkylation-carboxymethylation reaction.

Preparation of β-substituted γ-keto esters by the grignard reaction on N-acylpyrazoles

Various γ-keto esters were prepared by either the alcoholysis of N-(4-oxoalkanoyl)pyrazoles or the Grignard replacement of pyrazole moiety of 4-(N-pyrazolyl)-4-oxoalkanoic esters. By using 3-phenyl-ι-menthopyrazole as a chiral auxiliary, β-substituted γ-keto esters were enantioselectively obtained.

Palladium- and platinum-catalyzed reaction of siloxycyclopropanes with acid chlorides. A homoenolate route to 1,4-dicarbonyl compounds

1,4-Keto esters and 1,4-diketones have been synthesized by the palladium-catalyzed reaction of siloxycylopropanes and acid chlorides.

Reaction of 6-Phenyl-2-(p-toluenesulfonyl)-3(2H)pyridazinone with Grignard Reagents

6-Phenyl-2-(p-toluenesulfonyl)-3(2H)-pyridazinone (I) reacted with Grignard reagents to give 5-substituted 4,5-dihydro-3(2H)pyridazinones II and two types of dihydropyridazines, III and IV.The ratio of II, III, and IV was sensitively dependent on the reac