Recent Progress on Cu-Catalyzed Asymmetric Conjugate Borylation toα,β-Unsaturated Compounds
نویسندگان
چکیده
منابع مشابه
Cu(II)-catalyzed asymmetric boron conjugate addition to α,β-unsaturated imines in water.
Enantioselective conjugate addition of bis(pinacolato)diboron to α,β-unsaturated imines proceeds smoothly in water in the presence of a chiral copper(II) complex consisting of Cu(OAc)2 and chiral 2,2'-bipyridine. The corresponding β-boryl imines, which were oxidized to β-hydroxy imines, further leading to γ-amino alcohols, were obtained in high yields and high enantioselectivities.
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The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)2 and a chiral 2,2'-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis...
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Copper(I) has become the preferred metal to catalyze the β-boration of α,β-unsaturated carbonyl compounds, and now we demonstrate that easily accessible monodentate chiral ligands, such as phosphoramidites and phosphites, can be convenient alternative ligands to induce asymmetry in the enantioselective version of this reaction, particularly in the βboration of α,β-unsaturated imines. ■ INTRODUC...
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A series of chiral 6-membered ring N-heterocyclic carbene (NHC) precursors based on 3,4-dihydro-quinazoline were synthesized with overall yields of 54-62%. NHCs generated from these precursors show excellent asymmetric catalytic properties for borylation of α,β-unsaturated esters with enantioselectivity of up to 93% with a catalyst content of only 1 mol%.
متن کاملPalladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Cyclic Electrophiles.
This account describes our laboratory's efforts in the development of a palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic conjugate acceptors. Specifically, we highlight the study of this transformation in the following areas: (a) construction of all-carbon quaternary stereocenters, (b) elucidation of the reaction mechanism,
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ژورنال
عنوان ژورنال: Chinese Journal of Organic Chemistry
سال: 2015
ISSN: 0253-2786
DOI: 10.6023/cjoc201409019