Jaesook Yun

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.

We report an efficient and highly enantioselective hydroboration of aliphatic 1,1-disubstituted alkenes with pinacolborane using a phosphine-Cu catalyst. The method allows facile preparation of enantiomerically enriched β-chiral alkyl pinacolboronates from a range of 1,1-disubstituted alkenes with high enantioselectivity up to 99% ee. Unprecedented enantiodiscrimination between the geminal alkyl substituents was observed with functional group compatibility in the hydroboration. Furthermore, a ca

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.

A Cu-catalyzed highly Z-stereoselective hydroboration of alkynes with 1,8-naphthalenediaminatoborane (HB(dan)) is developed. DPEphos (bis[(2-diphenylphosphino)phenyl]ether)-ligated Cu catalysts produced alkenylboron compounds from terminal alkynes with excellent Z-stereoselectivity. In contrast, using a SIPr-CuCl complex as the precatalyst exclusively produced E-hydroboration products at mild conditions. Both catalytic procedures form alkenylboron products stereocomplementary to each other, cons

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

An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivit

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.