89359-12-6

Upstream product

• 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 
• 52449-43-1 (4-chloro-phenyl)-acetic acid methyl ester 
• 50415-59-3 methyl 2-(4-chlorophenyl)acrylate 
• 51747-43-4 2-(4-chlorophenyl)-acrylic acid 
• 89359-15-9 dimethyl (+)-(S)-2-(4-chlorophenyl)butane-1,4-dioate 
• 89358-85-0 ethyl 3C-(4-chlorophenyl)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate 

Downstream Products

• 89359-15-9 dimethyl (+)-(S)-2-(4-chlorophenyl)butane-1,4-dioate 

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.

Enantioselective Synthesis of Succinic Acids and γ-Lactones via Palladium Catalysed Allylic Substitution Reactions

The palladium catalyzed reaction between non-symmetrical allyl acetates and sodiodimethylmalonate proceeds in high yields and enantioselectivities (up to 99percent ee) using a diphenylphosphinoaryl oxazoline ligand.The so-formed substitution products are transformed into enantiomerically enriched succinic acids and also into enantiomerically enriched γ-lactones.

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.