329181-45-5

Upstream product

• 501-53-1 benzyl chloroformate 
• 63888-21-1 benzyl 3-phenyl-2-propynoate 
• 536-74-3 phenylacetylene 
• 1196-67-4 (E)-β-methylcinnamaldehyde 
• 100-51-6 benzyl alcohol 
• 71338-71-1 benzyl (E)-2-butenoate 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands

A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer.

Enantioselective Hydroamidation of Enals by Trapping of a Transient Acyl Species

An enantioselective synthesis of β-chiral amides through asymmetric and redox-neutral hydroamidation of enals is reported. In this reaction, a chiral N-heterocyclic carbene (NHC) catalyst reacts with enals to generate the homoenolate intermediate. Upon highly enantioselective β-protonation through proton-shuttle catalysis, the resulting azolium intermediate reacts with imidazole to yield the key β-chiral acyl species. This transient intermediate provides access to diversified β-chiral carbonyl derivatives, such as amides, hydrazides, acids, esters, and thioesters. In particular, β-chiral amides can be prepared in excellent yield and ee (40 chiral amides, up to 95 % yield and 99 % ee). This modular strategy overcomes the challenge of disruption of the highly selective proton-shuttling process by basic amines.

Potassium trifluoro(organo)borates in rhodium-catalyzed 1,4-additions to α,β-unsaturated esters

This letter describes an efficient and enantioselective conjugate addition of highly stable potassium trifluoro(organo)borates to α,β- unsaturated esters. This reaction, catalyzed by chiral rhodium(I) complexes, affords Michael adducts with high yields an

Asymmetric conjugate 1,4-addition of arylboronic acids to α,β-unsaturated esters catalyzed by rhodium(I)/(S)-binap

Arylboronic acids underwent the conjugate 1,4-addition to α,β-unsaturated esters to give β-aryl esters in high yields in the presence of a rhodium(I) catalyst. The addition of arylboronic acids to isopropyl crotonate resulted in high yields and high enantioselectivity exceeding 90% ee in the presence of 3 mol % of Rh(acac)(C2H4)2 and (S)-binap at 100 °C. The rhodium/(S)-binap complex provided (R)-3-phenylbutanoate in the addition of phenylboronic acid to benzyl crotonate. The effects on the enantioselectivity of chiral phosphine ligands, rhodium precursors, and substituents on α,β-unsaturated esters are discussed, as well as the mechanistic aspect of the catalytic cycle.