1451929-18-2Relevant academic research and scientific papers
BORON-NITROGEN LIGAND WITH CHIRAL 1,2-ETHYLENEDIAMINE BACKBONE, AND PREPARATION METHOD AND USE THEREOF
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Paragraph 0087-0089, (2021/08/20)
A boron-nitrogen ligand with a chiral 1,2-ethylenediamine backbone, a preparing method and used thereof are provided. The structural formula of the boron-nitrogen ligand is as shown in formula (I): wherein R1, R2 and R3 ar
A new chiral C1-symmetric NHC-catalyzed addition to α-aryl substituted α,β-disubstituted enals: Enantioselective synthesis of fully functionalized dihydropyranones
Lu, Hong,Liu, Jin-Yu,Li, Chen-Guang,Lin, Jun-Bing,Liang, Yong-Min,Xu, Peng-Fei
supporting information, p. 4473 - 4476 (2015/03/18)
The first enantioselective NHC-catalyzed activation of α-aryl substituted α,β-disubstituted unsaturated aldehyde is successfully developed via a highly-active acyl azolium intermediate. The new C1-symmetric biaryl-saturated imidazolium exhibits a superior ability to enable previously unavailable transformation, and the corresponding fully functionalized dihydropyranones are efficiently synthesized in high yields with excellent enantioselectivities. This journal is
Catalytic Asymmetric Hydroalkenylation of Vinylarenes: Electronic Effects of Substrates and Chiral N-Heterocyclic Carbene Ligands
Ho, Chun-Yu,Chan, Chun-Wa,He, Lisi
supporting information, p. 4512 - 4516 (2015/04/14)
An asymmetric tail-to-tail cross-hydroalkenylation of vinylarenes with terminal olefins was achieved by catalysis with NiH complexes bearing chiral N-heterocyclic carbenes (NHCs). The reaction provides branched gem-disubstituted olefins with high enantioselectivity (up to 94% ee) and chemoselectivity (cross/homo product ratio: up to 99:1). Electronic effects of the substituents on the vinylarenes and on the N-aryl groups of the NHC ligands, but not a π,π-stacking mechanism, assist the steric effect and influence the outcome of the cross-hydroalkenylation.
Chiral NHC/Cu(I)-catalyzed asymmetric hydroboration of aldimines: Enantioselective synthesis of α-Amido boronic esters
Zhang, Shu-Sheng,Zhao, Yi-Shuang,Tian, Ping,Lin, Guo-Qiang
supporting information, p. 437 - 442 (2013/03/29)
Non-Csymmetric (N-alkyl, N-aryl)-hybrid chiral NHC/Cu(I) complex catalyzed asymmetric hydroboration of N-benzoyl aldimines has been developed. The reaction proceeded smoothly at room temperature, giving α-amido boronic esters in excellent yields (up to 94
Copper-free asymmetric allylic alkylation with a grignard reagent: Design of the ligand and mechanistic studies
Grassi, David,Dolka, Chrysanthi,Jackowski, Olivier,Alexakis, Alexandre
supporting information, p. 1466 - 1475 (2013/02/25)
The Cu-free asymmetric allylic alkylation, catalysed by NHC, with Grignard reagents is reported on allyl bromide derivatives with good results. The enantioselectivity was quite homogeneous (around 85 % ee) on large and various substrates, regardless of the nature of the Grignard reagent. The formation of stereogenic quaternary centres was highly regioselective for both aliphatic and aromatic derivatives with good enantiomeric excess (up to 92 % ee). The methodology developed was found to be complementary with the Cu-catalysed version. Several new NHCs were tested with improved efficiency. In addition, mechanistic studies, using NMR spectroscopy, led to the discovery of the catalytically active species. Copyright
NHC-Cu-catalyzed enantioselective hydroboration of acyclic and exocyclic 1,1-disubstituted aryl alkenes
Corberan, Rosa,Mszar, Nicholas W.,Hoveyda, Amir H.
supporting information; experimental part, p. 7079 - 7082 (2011/09/30)
Tough nut to crack: Chiral bidentate N-heterocyclic carbene copper complexes were designed that promote enantioselective hydroborations of one of the most difficult substrate classes: acyclic and exocyclic 1,1-disubstituted alkenes undergo reaction with >98% site selectivity, in up to >98% yield and e.r=96.5:3.5 (see scheme, B2(pin)2 = bis(pinacolato)diboron). Copyright
Monodentate non-C2-symmetric chiral N-heterocyclic carbene complexes for enantioselective synthesis. Cu-catalyzed conjugate additions of aryl- and alkenylsilylfluorides to cyclic enones
Lee, Kang-Sang,Hoveyda, Amir H.
supporting information; experimental part, p. 4455 - 4462 (2009/09/30)
(Chemical Equation Presented) A new class of enantioselective conjugate addition (ECA) reactions that involve aryl- or alkenylsilyl fluoride reagents and are catalyzed by chiral non-C2-symmetric Cu-based N-heterocyclic carbene (NHC) complexes a
