189884-50-2

Upstream product

• 81701-30-6 (E)-4-methoxycinnamyl acetate 
• 18424-76-5 sodiodimethylmalonate 
• 108-59-8 malonic acid dimethyl ester 
• 496789-06-1 (E)-p-methoxycinnamyl methyl carbonate 
• 488151-80-0 3-(p-methoxyphenyl)-2-propen-1-yl methyl carbonate 
• 18424-76-5 dimethyl malonate sodium salt 

Downstream Products

• 107985-97-7 (4R)-(-)-4-(4-methoxyphenyl)tetrahydro-2H-pyran-2-one 
• 918149-72-1 (S)-3-(p-methoxyphenyl)-4-pentenoic acid 

Relevant academic research and scientific papers

Iridium/ N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction

N-Heterocyclic carbenes (NHCs) were found to be suitable ligands in Ir-catalyzed intermolecular allylic alkylation reaction. In the presence of a catalyst derived from [Ir(dncot)Cl]2 (dncot = dinaphthocyclooctatetraene) and triazolium salt L7,

Synthesis of 1-[bis(trifluoromethyl)phosphine]-1'- oxazolinylferrocene ligands and their application in regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates

A class of novel, easily accessible and air-stable 1-[bis(trifluoromethyl) phosphine]-1'-oxazolinylferrocene ligands has been synthesized from ferrocene. It became apparent that these ligands can be used in the regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates in a highly efficient manner. Excellent regio- and enantioselectivity could be obtained for a wide range of substrates.

Iridium-catalyzed allylic alkylation reaction with N-aryl phosphoramidite ligands: Scope and mechanistic studies

A series of N-aryl phosphoramidite ligands has been synthesized and applied to iridium-catalyzed allylic alkylation reactions, offering high regio- and enantioselectivities for a wide variety of substrates. These ligands feature the synthetic convenience and good tolerance of the ortho-substituted cinnamyl carbonates. Mechanistic studies, including DFT calculations and X-ray crystallographic analyses of the (π-allyl)-Ir complexes, reveal that the active iridacycle is formed via C(sp2)-H bond activation.

Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (-)-paroxetine

An Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxide is described. Asymmetric allylic alkylation of terminal allylic carbonates proceeded using 5 mol % of Ir catalyst, 5 mol % of DIAPHOX 1i, 10 mol % of NaPF6, 10 mo

Phosphoramidite ligands in iridium-catalyzed allvlic substitution

A new phosphoramidite ligand was used in the iridium-catalyzed allylic substitution reaction. This permitted high regio- and enantioselectivities on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resolution reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics was explored in detail, as was the role of the substituent in the ortho-position of the amine moiety.

Conformational preferences and enantiodiscrimination of phosphino-4-(1-hydroxyalkyl)oxazoline-metal-olefin complexes resulting from an OH-metal hydrogen bond

Phosphinooxazolines carrying (1-hydroxy-1-phenyl)methyl and (1-methoxy-1-phenyl)methyl substituents in the 4 position of the oxazoline ring exhibit contrasting behavior in Pd- and Ir-catalyzed allylic alkylations. Whereas catalysts with the methoxy-containing ligand generally provide products with high ee's, use of catalysts prepared from the hydroxy-containing ligand results in products with low ee's or even racemates. DFT calculations suggest the presence of a hydrogen bond with Pd(0) as the proton acceptor in the hydroxy-containing olefin-Pd(0) complexes, which induces a conformational change in the ligand, leading to different stereoselectivity.

Enantioselective allylic substitution, of cinnamyl esters catalyzed by iridium - Chiral aryl phosphite complexs conspicuous change in the mechanistic spectrum by a countercation and solvent

Indium-catalyzed asymmetric allylic alkylation of monoaryl substrates 4-6 with chiral phosphites 1-3 has been investigated. Although branched isomers were formed with high regioselectivities, the enantioselectivities of these products were remarkably influenced by solvents, countercations, and additives (ZnCl2 and LiCl).

Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylation

(Chemical Equation Presented) Linear or branched allylic carbonates or acetates undergo enantioselective iridium-catalyzed allylic substitution with sodium malonate. The reaction is wide in scope and affords the branched product in high yield and with hig

Regio- and enantioselective iridium-catalyzed allylic alkylation with in situ activated P,C-chelate complexes

Come together: Successful cooperation of iridium and copper yielded a new catalyst system for allylic alkylation. Branched alkylation products can be obtained rapidly and with high enantioselectivity from simple linear precursors (see scheme; cod = cycloo