Sungkyunkwan University · Chemistry
Professor Jaesook Yun's research lab specializes in the development of transition metal-catalyzed borylation and hydrosilylation reactions, with a strong focus on asymmetric synthesis and regioselective transformations of unsaturated carbon–carbon bonds. The lab pioneers innovative copper- and titanium-based catalytic systems for the efficient synthesis of alkenylboronic esters and chiral alcohols, emphasizing high enantio- and diastereoselectivity. Their work centers on designing novel ligands and catalysts to enable selective borylcupration of alkynes and alkenes, contributing to the synthesis of versatile organoboron and organosilicon intermediates for pharmaceutical and fine chemical applications.
Figures are computed from collected data and may differ slightly.
A bisphosphine/copper catalyst was used for the asymmetric hydroboration of 1,8-naphthalenediaminatoboryl (Bdan) substituted alkenes (see scheme; pin=pinacolato). Simple alkyl-substituted borylalkenes and styrene derivatives were hydroborated with high regio- and enantioselectivity. The electronic and steric properties of the Bdan group significantly affected the reactivity and regioselectivity of hydroboration. As a service to our authors and readers, this journal provides supporting informatio
The efficient copper-catalyzed addition reaction of bis(pinacolato)diboron to alpha,beta-acetylenic esters has been developed, which produces the corresponding beta-borylated-alpha,beta-ethylenic esters in high yields under mild reaction conditions.
The efficient asymmetric hydrosilylation of ketones with a chiral titanocene catalyst has been realized. In this procedure, (R,R)-ethylenebis(tetrahydroindenyl) titanium difluoride (1) was used as the precatalyst, and alcohol additives were employed. Aromatic and α,β-unsaturated ketones were reduced to the corresponding alcohols with a high level of enantioselectivity.
New catalytic systems based on a bis(1,3-disubstituted imidazoline 2-thione)-copper complex have been developed for the highly regioselective boration of internal alkynes.
Correction for 'Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes' by Hye Ryung Kim et al., Chem. Commun., 2011, 47, 2943-2945.
Abstract The development of catalytic Cu‐B additions to carbon–carbon unsaturated bonds (borylcupration) with high regio‐ and stereoselectivity has enabled facile and direct syntheses of alkenylboronic esters, which are versatile synthetic intermediates in organic synthesis. An increasing number of relevant reactions have been reported over the past several years, which can be categorized based on the electrophilic reagent that reacts with the common alkenylcopper intermediates that are generate
The highly enantioselective conjugate boration of six-membered and seven-membered cyclic enones and unsaturated esters was achieved by the use of a copper-(R,S)-Taniaphos complex with up to 99% ee under optimal conditions.
Easy access: The highly enantioselective conjugate reduction of α,β-unsaturated nitriles is achieved by employing bench-top stable copper(II) acetate and josiphos (L) as the ligand in the presence of polymethylhydrosiloxane (PMHS). This protocol provides ready access to valuable chiral β-aryl substituted nitriles in good yields and with excellent enantioselectivities.
The pinacol of ligands: The (R)-DTBM-Segphos coordinated copper(I) complex was found to be very effective for the asymmetric hydroboration of β-substituted styrene derivatives with pinacolborane (see scheme; DTBM=3,5-di-tert-butyl-4-methoxyphenyl). This new method affords benzylic pinacol boronate esters with excellent levels of regio- and enantioselectivity (>99 %). Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, bu
Challenging tertiary organoboronic esters containing a β-ester group were prepared enantioselectively via the asymmetric conjugate boration of β,β-disubstituted α,β-unsaturated esters with a copper–phosphine catalyst (see scheme). The functionalized organoboron derivatives can be utilized as a carbon nucleophile to form all-carbon quaternary centers. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited
Abstract The highly enantioselective reduction of imines is achieved by employing chiral Zn/diamine catalysts. This new catalytic protocol offers attractive features such as use of a non‐precious metal and an inexpensive silane, easy modification of chiral diamine ligands and provides ready access to chiral amines in good yields and with excellent enantioselectivities.
Kinetic resolution of the N-methyl imines of 3-substituted indanones and 4-substituted tetralones could be accomplished by hydrosilylation with a chiral titanocene catalyst. N-Methyl imines of 4-substituted tetralones were resolved to yield, after hydrolysis of the unreacted starting materials, ketones with high ee's and the amine products with high diastereomeric and enantiomeric purity. The utility of this process was demonstrated in the synthesis of sertraline.
A new, air stable and well-defined carbene-copper(II) complex has been prepared, which is an efficient precatalyst for the 1,2- and 1,4-reduction of carbonyl compounds under hydrosilylation conditions.
The copper-catalyzed sequential hydroboration of terminal alkynes with pinacolborane to prepare 1,1-diborylalkanes directly from alkynes was studied. Protected propargyl amines, propargyl alcohol derivatives, and simple alkynes regioselectively produced the desired 1,1-diborylalkanes in good yields with a copper/xantphos catalyst.
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