14366-99-5

Upstream product

• 186581-53-3 diazomethane 
• 34239-38-8 (2R,3R)-3-Hydroxy-2-methyl-3-phenyl-butyric acid 
• 554-12-1 propanoic acid methyl ester 
• 98-86-2 acetophenone 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 106836-55-9 (E)-4-Methyl-5-oxo-5-phenyl-3-pyrrolidin-1-yl-pent-2-enoic acid methyl ester 
• 292638-85-8 acrylic acid methyl ester 
• 106836-52-6 (5S,6S)-5-Methyl-6-phenyl-4-pyrrolidin-1-yl-5,6-dihydro-pyran-2-one 

Downstream Products

• 84466-76-2 3-Hydroxy-2-methyl-3-phenyl-thiobutyric acid S-pyridin-2-yl ester 
• 84466-77-3 2-Methyl-3-methylsulfanylmethoxy-3-phenyl-thiobutyric acid S-pyridin-2-yl ester 
• 84466-78-4 2-Methyl-3-methylsulfanylmethoxy-1,3-diphenyl-butan-1-one 
• 84466-77-3 2-Methyl-3-methylsulfanylmethoxy-3-phenyl-thiobutyric acid S-pyridin-2-yl ester 
• 84466-78-4 2-Methyl-3-methylsulfanylmethoxy-1,3-diphenyl-butan-1-one 

Relevant academic research and scientific papers

Zinc Acetate Catalyzed Enantioselective Reductive Aldol Reaction of Ketones

A highly enantioselective method for the synthesis of β-hydroxy esters via reductive aldol reaction of acrylates with aryl and heteroaromatic ketones is described. In situ generated catalyst composed of zinc acetate and chiral diamine afforded enantioenri

Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

The Mukaiyama aldol reaction is a widely applied carbon–carbon bond forming reaction. However, despite numerous well-established methods using aldehydes as acceptors, only few examples exist with ketones. Here we report a highly practical catalytic approach to this transformation, namely, the triflimide catalyzed Mukaiyama aldol reaction of silyl ketene acetals with ketones. This method exhibits a broad substrate scope, is very rapid, tolerates functionalized substrates, and requires only parts-per-million catalyst loadings with preparative scale reactions up to hundreds of grams in excellent purity (>99 %).

Copper hydride-catalyzed conjugate reduction-aldol addition domino reaction of α,β-unsaturated carboxylates with ketones

Copper hydride-catalyzed conjugate reduction-intermolecular aldol addition domino reactions were realized using α,β-unsaturated carboxylates as hydride acceptors and a silane as the reducing reagent. High diastereoselectivities were achieved with 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene as the ligand and tert-butyl acrylate as the hydride acceptor. Copper hydride ligated with DPEphos or Xantphos ligand could catalyze conjugate reductive intermolecular aldol addition domino reactions of α,β- unsaturated carboxylates with ketones using a silane as the reducing reagent. High diastereoselectivities were achieved using tert-butyl acrylate as the hydride acceptor in the presence of Xantphos.

Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters

Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating groups.

Iron-catalysed Reformatsky-type reactions

A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloro

Iron-mediated electrochemical reaction of α-chloroesters with carbonyl compounds

(Matrix presented) Reformatsky-type reactions have been performed efficiently using an electroassisted iron-complex catalysis. Valuable product such as β-hydroxyesters, ketones or nitriles are thus prepared with high yields.

A New Protocol for the Diastereoselective Formation of Lactones from either Achiral or Chiral Vinylogous Urethanes

The condensations of vinylogous urethanes, with or without a chiral auxiliary, and a variety of acid chlorides are described.Treatment of these acylated products with either L-Selectride or organometallic reagents leads, with high diastereoselectivity, to lactone products.

Synthesis and Proton Nuclear Magnetic Resonance Spectra of Diastereomeric β-Hydroxy Esters. An Unusual Hydroxy to Methyl Coupling through Four ? Bonds

A series of 3-hydroxy-3-phenyl-2-alkylbutyrate esters has been prepared by the reaction of various ester enolates with acetophenone.A 1:1 mixture of diastereoisomers was obtained in each case which was conveniently separated by HPLC.The two isomers, erythro (e) or threo (t), were identified on the basis of their IR and NMR spectra.In CDCl3 solution only the erythro isomers exhibited a 1-Hz coupling constant between the hydroxyl and geminal methyl protons.This coupling is transmitted through four ? bonds which are arranged in a "W" configuration.In Me2SO solution,the intramolecular hydrogen bond which allows the "W" configuration is disrupted, causing coupling to disappear and the spectra of the erythro and threo isomers to become nearly equivalent.