61423-03-8

Upstream product

• 73922-81-3 4-phenyl-but-3-yn-2-ol 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 536-74-3 phenylacetylene 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 108-22-5 Isopropenyl acetate 
• 75-36-5 acetyl chloride 
• 5876-76-6 (R)-4-phenylbut-3-yn-2-ol 

Downstream Products

• 100017-26-3 (R)-(Z)-3-acetoxy-1-phenyl-1-butene 
• 5876-76-6 (R)-4-phenylbut-3-yn-2-ol 
• 17488-65-2 (R)-(Z)-3-hydroxy-1-phenyl-1-butene 

Relevant academic research and scientific papers

Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation

N-(α-Hydroxyacyl)-glycinesters can be used as excellent nucleophiles in Pd-catalyzed allylic alkylation. The method allows for the stereoselective introduction of a wide range of side chains, including highly functionalized ones. Both diastereomers can be accessed through variation of the reaction conditions. Furthermore, the use of stannylated carbonates introduces vinylstannane motifs, which are eligible for subsequent C-C coupling reactions.

Dual enzymatic dynamic kinetic resolution by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase and Candida antarctica lipase B

The immobilization of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (TeSADH) using sol-gel method enables its use to racemize enantiopure alcohols in organic media. Here, we report the racemization of enantiopure phenyl-ring-containing secondary alcohols using xerogel-immobilized W110A TeSADH in hexane rather than the aqueous medium required by the enzyme. We further showed that this racemization approach in organic solvent was compatible with Candida antarctica lipase B (CALB)-catalyzed kinetic resolution. This compatibility, therefore, allowed a dual enzymatic dynamic kinetic resolution of racemic alcohols using CALB-catalyzed kinetic resolution and W110A TeSADH-catalyzed racemization of phenyl-ring-containing alcohols.

Kinetic resolution of secondary alcohols by chiral dmap derivatives prepared by the Ugi multicomponent reaction

The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the a-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s -factor of up to 12.

Hydrophosphination of propargylic alcohols and amines with phosphine boranes

The first uncatalyzed hydrophosphinations of propargylic amines and alcohols with phosphine- borane complexes are described. The reactions proceed at ambient temperature or below without the use of protecting groups or the need to handle pyrophoric second

Kinetic resolution of secondary alcohols by the combination of a chiral Br?nsted acid, DABCO, and acetyl chloride

An efficient and simple protocol for the kinetic resolution of secondary alcohols is presented. The new system is based on a combination of chiral Br?nsted acid, DABCO, and acetyl chloride and gives various enantioenriched alcohols with selectivity factors up to 105.

Developing asymmetric iron and ruthenium-based cyclone complexes; Complex factors influence the asymmetric induction in the transfer hydrogenation of ketones

The preparation of a range of asymmetric iron and ruthenium-cyclone complexes, and their application to the asymmetric reduction of a ketone, are described. The enantioselectivity of ketone reduction is influenced by a single chiral centre in the catalyst, as well as by the planar chirality in the catalyst. This represents the first example of asymmetric ketone reduction using an iron cyclone catalyst.

Synthesis of highly substituted allylic alcohols by a regio- and stereo-defined CuCl-mediated carbometallation reaction of 3-aryl-substituted secondary propargylic alcohols with Grignard reagents

A highly regio- and stereoselective CuCl-mediated carbometallation reaction of 3-aryl-substituted secondary propargylic alcohols with alkyl, aryl, vinyl or allyl Grignard reagents for the synthesis of fully-substituted allylic alcohols was developed. The R2 group from the Grignard reagent was successfully introduced to the 2-position of the propargylic alcohols due to the chelation of metal atom with the hydroxyl oxygen atom forming 5-membered metallacyclic intermediates, which smoothly react with various electrophiles to afford stereodefined polysubstituted allylic alcohols. By this method, optically active allylic alcohols can be prepared from readily available optically active propargylic alcohols without obvious racemization. Five-membered lactones can also be synthesized by Pd-catalyzed carbonylation with iodoallylic alcohols. The Royal Society of Chemistry 2009.

Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature

Aminocyclopentadienyl ruthenium complexes, which can be used as room-temperature racemization catalysts with lipases in the dynamic kinetic resolution (DKR) of secondary alcohols, were synthesized from cyclopenta-2,4-dienimines, Ru3(CO)12, and CHCl 3: [2,3,4,5-Ph4(η5-C 4CNHR)]Ru-(CO)2Cl (4: R = i-Pr; 5: R = n-Pr; 6: R = t-Bu), [2,5-Me2-3,4-Ph2(η5-C 4CNHR)]Ru(CO)2Cl (7: R = i-Pr; 8: R = Ph), and [2,3,4,5-Ph4(η5-C4CNHAr)]Ru(CO) 2Cl (9: Ar =p-NO2C6H4; 10: Ar = p-ClC6H4; 11: Ar = Ph; 12: Ar = p-OMeC6H 4; 13: Ar = p-NMe2C6H4). The tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In mechanistic studies for the catalytic racemization, ruthenium hydride 14 appeared to be a key species. It was the major organometallic species in the racemization of (S)-1-phenylethanol with 4 and potassium tert-butoxide. In a separate experiment, (S)-1-phenylethanol was racemized catalytically by 14 in the presence of acetophenone.

Chelated enolates of amino acid esters - New and efficient nucleophiles for isomerization-free, stereoselective palladium-catalyzed allylic substitutions

Chelated amino acid ester enolates were found to be suitable nucleophiles for palladium-catalyzed allylic alkylations. Unlike stabilized soft nucleophiles, the chelated enolates react under very mild reaction conditions, even at -78 °C. If TFA protected a