39520-67-7

Upstream product

• 1462-75-5 3-phenylpropylmagnesium bromide 
• 107-19-7 propargyl alcohol 
• 1256667-67-0 2-methylene-5-phenylpentanal 
• 103-63-9 1-phenyl-2-bromoethane 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 6683-49-4 (4-methylpent-4-en-1-yl)benzene 

Relevant academic research and scientific papers

Dehydrative/decarboxylative coupling of carboxylic acids with allylic alcohols

Herein reported is a dehydrative/decarboxylative coupling reaction of carboxylic acids with allylic alcohols, which is cocatalyzed by photoredox and palladium catalysts. α-Hetero- or aryl-substituted carboxylic acids and allylic alcohols, which are both readily available, directly participate in CC bond formation without any functional group transformation.

Enantioselective Reductive Divinylation of Unactivated Alkenes by Nickel-Catalyzed Cyclization Coupling Reaction

Catalytic asymmetric dicarbofunctionalization of tethered alkenes has emerged as a promising tool for producing chiral cyclic molecules; however, it typically relies on aryl-tethered alkenes to form benzene-fused compounds. Herein, we report an enantioselective cross-electrophile divinylation reaction of nonaromatic substrates, 2-bromo-1,6-dienes. The approach thus offers a route to new chiral cyclic architectures, which are key structural motifs found in various biologically active compounds. The reaction proceeds under mild conditions, and the use of chiral t-Bu-pmrox and 3,5-difluoro-pyrox ligands resulted in the formation of divinylated products with high chemo-, regio-, and enantioselectivity. The method is applicable for the incorporation of chiral hetero- and carbocycles into complex molecules.

Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration

Chiral boronic esters are useful intermediates in asymmetric synthesis. We have previously shown that carbonyl-directed catalytic asymmetric hydroboration (CAHB) is an efficient approach to the synthesis of functionalized primary and secondary chiral boronic esters. We now report that the oxime-directed CAHB of alkyl-substituted methylidene and trisubstituted alkene substrates by pinacolborane (pinBH) affords oxime-containing chiral tertiary boronic esters with yields up to 87 % and enantiomeric ratios up to 96:4 e.r. The utility of the method is demonstrated by the formation of chiral diols and O-substituted hydroxylamines, the generation of quaternary carbon stereocenters through carbon-carbon coupling reactions, and the preparation of chiral 3,4,4-trisubstituted isoxazolines.

Highly Regioselective Palladium-Catalyzed Carboxylation of Allylic Alcohols with CO2

Various allylic alcohols were carboxylated in the presence of a catalytic amount of PdCl2 and PPh3 using ZnEt2 as a stoichiometric transmetalation agent under a CO2 atmosphere (1atm). This carboxylation proceeded in a highly regioselective manner to afford branched carboxylic acids predominantly. The β,γ-unsaturated carboxylic acid thus obtained was successfully converted into an optically active γ-butyrolactone, a known intermediate of (R)-baclofen.