88057-04-9

Basic information

• Product Name: (S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester
• Synonyms: (S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester
• CAS NO: 88057-04-9
• Molecular Weight: 262.306
• Mol File: 88057-04-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester(88057-04-9)
• EPA Substance Registry System: (S,E)-2-(1-methyl-3-phenyl-allyl)malonic acid dimethyl ester(88057-04-9)

Safety Data

• Hazardous Substances Data: 88057-04-9(Hazardous Substances Data)

Upstream product

• 82045-04-3 (rac)-(E)-2-acetoxy-4-phenylbut-3-ene 
• 108-59-8 malonic acid dimethyl ester 
• 591-50-4 iodobenzene 
• 1313878-08-8 (S,E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl acetate 
• 18424-76-5 sodiodimethylmalonate 
• 62413-47-2 (2R,3E)-4-phenyl-3-buten-2-ol 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 81176-43-4 (S)-4-phenyl-but-3-en-2-ol 
• 95190-90-2 (2S)-(4-phenylbut-3-en-2-yl) N-phenylbenzimidate 
• 18424-76-5 dimethyl malonate sodium salt 
• 100017-26-3 (R)-(Z)-3-acetoxy-1-phenyl-1-butene 
• 121232-23-3 (+)-(R)-(E)-(4-phenyl-3-buten-2-yl) (diphenylphosphino)acetate 

Downstream Products

• 1310827-45-2 dimethyl 2-methyl-2-((E)-4-phenylbut-3-en-2-yl)malonate 

Relevant articles and documents

Palladium-catalyzed enantioselective allylic substitution in the presence of monodentate furanoside phosphoramidites

A library of monodentate furanoside phosphoramidites, easily synthesized from inexpensive D-xylose and optically pure 1,1-bi-2-naphthol (BINOL), was used as ligands for the palladium-catalyzed allylic alkylation and amination. The matched pair was formed from D-xylose-derivatives and (S)-BINOL. The asymmetric induction depends strongly on the substituent at the C5 of the carbohydrate backbone; both bulky 5-O-pivaloyl and 5-deoxy derivatives gave excellent results, whereas ligands with trityl protection at position C5 induced low ee values with reversal of configuration. The solvent used for the addition is also of great importance with highest enantioselectivities observed in diethyl ether. The best results for both alkylation and amination, up to 98-99 ee, were obtained for sterically demanding allylic acetates. Single is better: New carbohydrate ligands bearing a single 1,1-bi-2-naphthol (BINOL)-derived phosphoramidite moiety are developed and successfully applied to the palladium-catalyzed asymmetric allylic substitution. The enantioselectivities are equal or better than those obtained for similar systems containing two BINOL moieties and reach up to 99 ee.

Novel O,N,N,O-tetradentate ligand from tartaric acid

A new class of highly stable O,N,N,O-tetradentate bioxazoline ligands were synthesized from l-tartaric acid. Exploration of those ligands in Pd-catalyzed asymmetric allylic alkylation yielded alkylated product up to 96% ee. Necessity of additional chelation to obtain high enantioselectivity was also demonstrated. Structural modifications of this ligand might result in identification of a novel privileged chiral ligand from an inexpensive chiral pool.

Effective chiral ferrocenyl phosphine-thioether ligands in enantioselective palladium-catalyzed allylic alkylations

Chiral ferrocene-derived phosphine-thioether mixed donor ligands supported by heterocycles effected the palladium-catalyzed enantioselective allylic alkylations with excellent yields and enantioselectivities (up to 96% ee). With cyclic and unsymmetrical a