89359-15-9

Upstream product

• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 50415-59-3 methyl 2-(4-chlorophenyl)acrylate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 51747-43-4 2-(4-chlorophenyl)-acrylic acid 
• 1073-67-2 4-vinylbenzyl chloride 
• 186581-53-3 diazomethane 
• 89359-12-6 (+)-(S)-2-(4-chlorophenyl)butane-1,4-dioic acid 
• 89358-85-0 ethyl 3C-(4-chlorophenyl)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate 
• 89359-13-7 3-(4-chlorophenyl)-4-hydroxybutyro-1,4-lactone 
• 7270-47-5 4-chlorophenylmagnesium iodide 
• 89358-94-1 3C-(4-chlorophenyl)-2,3-dideoxy-D-manno-heptono-1,4-lactone 

Downstream Products

• 89359-12-6 (+)-(S)-2-(4-chlorophenyl)butane-1,4-dioic acid 

Relevant academic research and scientific papers

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

A thiourea-oxazoline library with axial chirality: Ligand synthesis and studies of the palladium-catalyzed enantioselective bis(methoxycarbonylation) of terminal olefins

We report herein the synthesis of novel chiral S,N-heterobidentate thiourea-oxazoline ligands and their application to palladium-catalyzed enantioselective bis(methoxycarbonylation)s of terminal olefins under mild conditions. Copper salts were found to play multiple roles in this reaction. Substituted 2- phenylsuccinates were obtained in >90% yield and up to 84% ee under optimized conditions.

Asymmetric Synthesis. Part 6. Copper Salt promoted Grignard Reagent Additions to Ethyl 2,3-Dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate and subsequent Formation of Optically Active 2-Alkyl (or Aryl) Butane-1,4-dioic Acids and Butyro-1,4-lactones

The copper-salt promoted 1,4-additions of aryl and t-butyl Grignard reagents to ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate are highly stereoselective yielding products with the D-manno-configuration.In contrast isopropyl and ethyl Grignarg reagents give products preponderantly with the D-gluco-configuration.Cyclohexylmagnesium bromide does not react stereoselectively but gives a 55:45 mixture of the D-gluco- and D-manno-isomers.Controlled degradation of the carbohydrate molecule affords 2-aryl (alkyl) butane-1,4-dioic acids and 3-aryl (alkyl)-butyro-1,4-lactones.The enantiomeric purity of these products is established by reference to known products or by use of optically active n.m.r. shift reagents.