872884-41-8

Upstream product

• 27301-54-8 (R)-(+)-pent-3-yn-2-ol 
• 58625-96-0 ethyl 2-methyl-2-pentenoate 
• 124306-44-1 (E)-2-methyl-1-phenyl-2-penten-1-one 
• 196702-57-5 Thioacetic acid S-(2-benzoyl-pentyl) ester 
• 872884-40-7 (S)-(+)-2-methyl-1-phenyl-4-penten-1-one 
• 90080-22-1 ((Z)-(R)-1-Methyl-but-2-enyloxymethyl)-benzene 
• 93-55-0 1-phenyl-propan-1-one 
• 79646-46-1 (R)-(-)-(Z)-pent-3-en-2-ol 
• 872884-20-3 (Z)-allyl (1-phenylprop-1-en-1-yl) carbonate 

Relevant academic research and scientific papers

Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones

Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.

Palladium-catalyzed decarboxylative asymmetric allylic alkylation of enol carbonates

Palladium-catalyzed decarboxylative asymmetric allylic alkylation (DAAA) of allyl enol carbonates as a highly chemo-, regio-, and enantioselective process for the synthesis of ketones bearing either a quaternary or a tertiary R-stereogenic center has been investigated in detail. Chiral ligand L4 was found to be optimal in the DAAA of a broad scope of cyclic and acyclic ketones including simple aliphatic ketones with more than one enolizable proton. The allyl moiety of the carbonates has been extended to a variety of cyclic or acyclic disubstituted allyl groups. Our mechanistic studies reveal that, similar to the direct allylation of lithium enolates, the DAAA reaction proceeds through an "outer sphere" S N2 type of attack on the π-allylpalladium complex by the enolate. An important difference between the DAAA reaction and the direct allylation of lithium enolates is that in the DAAA reaction, the nucleophile and the electrophile were generated simultaneously. Since the π-allylpalladium cation must serve as the counterion for the enolate, the enolate probably exists as a tight-ion-pair. This largely prevents the common side reactions of enolates associated with the equilibrium between different enolates. The much milder reaction conditions as well as the much broader substrate scope also represent the advantages of the DAAA reaction over the direct allylation of preformed metal enolates.

Highly enantioselective synthesis of optically active ketones by iridium-catalyzed asymmetric hydrogenation

(Chemical Equation Presented) Close to perfect enantioselectivity (up to 99% ee, see scheme) is found for the formation of α-substituted ketones by the asymmetric hydrogenation of enones with an iridium-phosphinooxazoline catalyst. In an operationally simple process, both linear and cyclic substrates react well and afford the desired products in high yields. A wide variety of substituents are tolerated, thus making the method synthetically appealing.

Palladium-catalyzed asymmetric allylic α-alkylation of acyclic ketones

The first example of Pd-catalyzed asymmetric allyl alkylation of the conformationally nonrigid acyclic ketone enolates is reported with excellent yields, regioselectivity, and enantioselectivity. The double bond geometry of the allyl enol carbonates affec

Syntheses of optically active γ-ketothiols and the esters by lipase-catalyzed hydrolysis via α-acetylthiomethylation of ketones

The α-acetylthiomethylation of ketones was achieved by the reaction of ketones or the enamines with N,N-bis-(acetylthiomethyl)-p-chloroaniline in the presence of trifluoroacetic acid. The resulting thiolesters were hydrolyzed enantioselectively by catalys

HIGHLY ENANTIOSPECIFIC AND ERYTHRO-SELECTIVE -WITTIG REARRANGEMENT OF ENANTIOMERICALLY ENRICHED ALLYLIC BENZYL ETHERS. A NEW, FORMAL CHIRAL SYNTHESIS OF l-EPHEDRINE

The -Wittig rearrangement of chiral (Z)-allylic benzyl ethers provides 94-97percent of asymmetric transfer (enantiospecificity), along with 90-96percent of erythro-selectivity.Its synthetic potential is illustrated through the stereocontrolled synthe