7210-42-6

Upstream product

• 6270-17-3 ethyl 3-benzoylpropanoate 
• 75-16-1 methylmagnesium bromide 
• 35959-54-7 4-hydroxy-4-phenyl-valeric acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 98-86-2 acetophenone 
• 123-25-1 succinic acid diethyl ester 
• 186581-53-3 diazomethane 
• 64-19-7 acetic acid 
• 98-83-9 isopropenylbenzene 
• 67-56-1 methanol 
• 88730-09-0 C₁₁H₁₂N₂O 
• 6051-52-1 2-phenylbut-3-en-2-ol 
• 201230-82-2 carbon monoxide 
• 17920-93-3 1-phenyl-6-methyl-5-hepten-2-ol 

Downstream Products

• 24459-27-6 2-methyl-5-phenylhexane-2,5-diol 
• 4408-55-3 4-methyl-4-phenylpentanoic acid 
• 51690-49-4 4-Methyl-4-phenyl-pentanoic acid methyl ester 
• 16433-43-5 4-phenyl-1-pentanoic acid 
• 20881-29-2 dihydro-α-norcurcumenic acid methylester 
• 35959-54-7 4-hydroxy-4-phenyl-valeric acid 
• 88730-04-5 4-Hydroxy-4-phenyl-pentanoic acid hydrazide 
• 88730-06-7 1-Amino-5-methyl-5-phenyl-pyrrolidin-2-one 
• 88730-09-0 C₁₁H₁₂N₂O 
• 88730-10-3 4-Hydroxy-4-phenyl-pentanoic acid dimethylamide 
• 88730-11-4 4-Methoxy-4-phenyl-pentanoic acid methyl ester 
• 53380-17-9 4,4-diphenyl-valeric acid 
• 99647-87-7 (+/-)-4-methyl-4-phenyl-3,4-dihydronaphthalen-1(2H)-one 

Relevant academic research and scientific papers

Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents

We report the development of a stereoselective method for the allylation of ketones utilizing N-substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtai

A Highly Efficient Asymmetric Synthesis of a 4,4-Disubstituted Butan-4-olide by the 1,7-Asymmetric Inductive Addition of Grignard Reagents to γ-Keto Esters

An efficient asymmetric synthesis of a butan-4-olide having a quarternary asymmetric carbon centre was achieved with up to 97percent enantiomeric excess (e.e.) by the 1,7-asymmetric inductive addition of Grignard reagents to the γ-keto esters 4-7, the e.e. of which was highly dependent on the structure of the chelating group of the chiral auxiliaries 1-3.

One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping

A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.

Development of Nitrolactonization Mediated by Iron(III) Nitrate Nonahydrate

The nitrolactonization of alkenyl carboxylic acids mediated by Fe(NO3)3·9H2O has been developed. Nitrolactones were obtained in up to 93% yield by treatment of alkenyl carboxylic acids with Fe(NO3)3·9H2O. Mechanistic studies disclosed that the reaction proceeded through a radical intermediate generated from addition of NO2 to alkenyl carboxylic acids.

ZnI2/Zn(OTf)2-TsOH: A versatile combined-Acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization

A mild and efficient combined-Acid system using a zinc(ii) salt [ZnI2 or Zn(OTf)2] and p-Toluene sulfonic acid (TsOH) was investigated for catalytic cationic cyclizations, including intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, hydroarylation and polyene cyclizations. This reaction provides easy access to five-and six-membered O-and N-containing saturated heterocyclic compounds, tetrahydronaphthalene derivatives and polycyclic skeletons in excellent yield with perfect Markovnikov selectivity and under mild conditions. The operational simplicity, broad applicability, and use of inexpensive commercially available catalysts make this protocol superior to existing methodologies.

Calcium(II)- And Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol

We report an efficient intramolecular hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist of reactivity observed between the hydroamidation and hydroacyloxylation of unactivated alkenes regarding the formation of 5- and 6-membered rings.

Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.

Nucleo-Palladation-Triggering Alkene Functionalization: A Route to γ-Lactones

An unprecedented strategy for the highly effective synthesis of γ-lactones from homoallylic alcohols was achieved by palladium catalysis in one step. The protocol affords aryl, alkyl, and spiro γ-lactones directly from readily available homoallylic alcohols in good yields with excellent functional group tolerance and high chemoselectivity under mild conditions.

MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones

An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.

Copper-Catalyzed Formal [2+2+1] Heteroannulation of Alkenes, Alkylnitriles, and Water: Method Development and Application to a Total Synthesis of (±)-Sacidumlignan D

A copper-catalyzed three-component reaction of alkenes, alkylnitriles, and water affords γ-butyrolactones in good yields. The domino process involves an unprecedented hydroxy-cyanoalkylation of alkenes and subsequent lactonization with the creation of three chemical bonds and a quaternary carbon center. The synthetic potential of this novel [2+2+1] heteroannulation reaction was illustrated by a concise total synthesis of (±)-sacidumlignan D.