949568-24-5

Upstream product

• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 528852-26-8 (E)-3-(4-methoxyphenyl)-3-phenylacrylic acid 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 496789-06-1 (E)-p-methoxycinnamyl methyl carbonate 
• 591-50-4 iodobenzene 
• 488151-80-0 3-(p-methoxyphenyl)-2-propen-1-yl methyl carbonate 
• 100-58-3 phenylmagnesium bromide 
• 85217-69-2 cinnamyl methyl carbonate 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 92804-32-5 3-(4-methoxyphenyl)-3-phenylpropanal 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes

The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.

Copper-catalyzed asymmetric allylic substitution of allyl phosphates with aryl- and alkenylboronates

The asymmetric allylic substitution of allyl phosphates with aryl- and alkenylboronates catalyzed by a copper/N-heterocyclic carbene complex was developed and the substitution products were obtained with high enantioselectivity (see scheme). To account for the observed influence of the reaction parameters a possible catalytic cycle for this process was proposed. Copyright

Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes

A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center with two different aryl groups with enantioselectivities of up to 91% ee.

Enantioselective iridium-catalyzed allylic arylation

We describe herein the development of the first iridium-catalyzed allylic substitution using arylzinc nucleophiles. High enantioselectivities were obtained from the reactions, which used commercially available Grignard reagents as the starting materials. This methodology was also shown to be compatible with halogen/metal exchange reactions. Its synthetic potential is demonstrated by its application towards the formal synthesis of (+)-sertraline.

Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents

Thanks to iridium catalysis, arylzinc reagents undergo regioselective allylic substitution with very high enantioselectivity, when associated with phosphoramidite ligands.

Highly enantioselective 1,4-addition of arylzinc reagents to 3-arylpropenals catalyzed by a rhodium-binap complex in the presence of chlorotrimethylsilane

Asymmetric 1,4-addition of arylzinc chlorides to (E)-3-arylpropenals proceeded with high enantioselectivity in the presence of a rhodium/(R)-binap catalyst and chlorotrimethylsilane to give, after hydrolysis, high yields of the corresponding 3,3-diarylpro