244221-60-1

Upstream product

• 21040-45-9 Cinnamyl acetate 
• 100-46-9 benzylamine 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 160879-62-9 methyl 1-phenylprop-2-enyl carbonate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 85217-69-2 cinnamyl methyl carbonate 

Downstream Products

• 1087162-44-4 (S)-(-)-N-benzyl-N-(1-phenylallyl)acetamide 
• 1284206-81-0 (3S,3aS)-2-benzyl-3-phenyl-2,3,3a,4-tetrahydrocyclopenta[c]pyrrol-5(1H)-one 
• 1284206-47-8 (1S)-N-benzyl-1-phenyl-N-(prop-2-yn-1-yl)prop-2-en-1-amine 

Relevant academic research and scientific papers

Superior performance of a chiral catalyst confined within mesoporous silica

A chiral catalyst from the ligand 1,1'-bis(diphenylphosphino)ferrocene (dppf) anchored to the inner walls of the mesoporous support MCM-41 and co-ordinated to Pd(II) has been shown to exhibit a degree of regioselectivity and enantiomeric excess, in the allylic amination of cinnamyl acetate, which is far superior to that of its homogeneous counterpart or that of a surface-bound analogue attached to a non-porous silica.

Rh(I)/Bisoxazolinephosphine-Catalyzed Regio- And Enantioselective Allylic Substitutions

Rhodium(I)/bisoxazolinephosphine combination has been developed as a general catalyst to achieve the dynamic kinetic asymmetric allylation of a variety of nitrogen, carbon, oxygen, and sulfur pronucleophiles from branched racemic allylic carbonates. Exclusive branch-selectivity and up to 99% enantiomeric excess could be obtained under neutral conditions. Linear allylic substrates (both Z and E) could be converted to the same chiral branched products with excellent regio- and enantioselectivities as well. Chiral π-allyl-Rh(III)/NPN intermediate was isolated and characterized to understand the origin of the high selectivities.

Containing dinaphthyl [1, 2-b; 5, 6-b '] chiral phosphine nitrogen skeleton and cyclooctatetraene π-ene propyl iridium complex, synthesis method and application

The invention provides an optically pure pi-allyl iridium complex containing dinaphthyl [1,2-b;5,6-b'] cyclooctatetraene and a chiral phosphine nitrogen framework as well as a synthesizing method and application of the complex in an asymmetric allyl subst

Immobilized catalysts for iridium-catalyzed allylic amination: Rate enhancement by immobilization

The first immobilized catalyst for Ir-catalyzed asymmetric allylic aminations is described. The catalyst is a cationic (π-allyl)Ir complex bound by cation exchange to an anionic silica gel support. Preparation of the catalyst is facile, and the supported

Substituent effects on the amination of racemic allyl carbonates using commercially available chiral rhodium catalysts

In the presence of commercially available chiral rhodium catalysts, a competitive benzy lamination of racemic allyl carbonates, substituted with p-X-Ph groups, shows that the reaction proceeds faster with substituents (X) that are more electron-withdrawing. Mechanistic implications of these results are discussed.

Highly regioselective allylic substitution reactions catalyzed by an air-stable (π-Allyl)iridium complex derived from dinaphthocyclooctatetraene and a phosphoramidite ligand

An air-stable (π-allyl)iridium complex derived from dinaphthocyclooctatetraene and a phosphoramidite ligand has been synthesized and found to be highly efficient in iridium-catalyzed allylic substitution reactions. This catalyst features excellent regiose

Helicene-based phosphite ligands in asymmetric transition-metal catalysis: Exploring Rh-catalyzed hydroformylation and Ir-catalyzed allylic amination

Starting from the optically pure [6]helicene-like alcohol(P,3S)-3-methyl-4- (4-methylphenyl)-1,3,6,7-tetrahydrobenzo[c]benzo[5,6]phenanthro[4,3-e] oxepin-14-ol, four helical phosphites were prepared from the corresponding chlorophosphites. These ligands containing parent or substituted 1,3,2-dioxaphospholan-2-yl or dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl moieties were applied to the asymmetric hydroformylation of terminal alkenes catalyzed by Rh(acac)(CO)2 and the asymmetric allylic amination of cinnamyl-type carbonates catalyzed by [Ir(cod)Cl]2. The helical phosphite containing the dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl group was most successful in the asymmetric hydroformylation of styrene, leading to moderate enantiomeric excess values (up to 32 % ee), high regioselectivity in favor of the branched product, and mostly high conversion, whereas the helical ligand containing the 4,4,5,5-tetramethyl-1,3,2-dioxaphospholan-2-yl fragment was most effective in asymmetric allylic aminations, exhibiting high enantioselectivity (up to 94 % ee), excellent regioselectivity in favor of the branched products, and good reactivity. This study represents the first use of helicene-like ligands in asymmetric reactions, including hydroformylation and allylic amination, and the promising results indicate the potential of the helicene moieties as chiral inductors. Copyright

Regio- and enantioselective allylic substitution with less active N- or O-nucleophiles catalyzed by iridium-complex of bis(oxazolinyl)pyridine

The utility of hydroxylamines as nitrogen nucleophiles was investigated in the iridium-catalyzed regio- and enantioselective allylic substitution. Allylic substitution with hydroxylamines proceeded with good enantioselectivities by using the iridium-complex of bis(oxazolinyl)pyridine ligand. The good regio- and enantioselectivities were also achieved in the reaction with alkylamines, p-anisidine, and 4-methoxyphenol.

A highly enantioselective allylic amination reaction using a commercially available chiral rhodium catalyst: Resolution of racemic allylic carbonates

A novel method for the kinetic resolution of unsymmetrical acyclic allylic carbonates and the concurrent synthesis of enantioenriched secondary amines using a commercially available chiral catalyst is disclosed.

Application of iridium catalyzed allylic substitution reactions in the synthesis of branched tryptamines and homologues via tandem hydroformylation- Fischer indole synthesis

Combination of enantioselective allylation reactions with a tandem hydroformylation-Fischer indole synthesis sequence as a highly diversity-oriented strategy for the synthesis of tryptamines and homologues was explored. This modular approach allows the su