Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

Shen, Tianhua; Qin, Quan; Ni, Hang; Xia, Ting; Zhou, Xiuqing; Cui, F.; Li, Junqi; Ran, De-qiang; Song, Qingbao

doi:10.3906/kim-1210-62

Cited by 4 publications

(2 citation statements)

References 17 publications

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“…The intermediate B then reacted with the triethylammonium acetate generated earlier to obtain the corresponding β-nitroalcohol product, and at the same time, a bivalent metal complex and a triethylamine molecule were released. According to the above experimental results and the reported literature [37][38][39], we managed to deduce the possible reaction mechanism of nitromethane with aromatic aldehydes in the presence of [ML(CH 3 COO) 2 (H 2 O) n ] (n = 1, M = Ni; n = 0, M = Zn) with 20 mol% Et 3 N as the co-catalyst. As shown in Figure 6, under the action of alkaline triethylamine, nitromethane was activated to coordinate to the bivalent metal cation in [ML(CH 3 COO) 2 (H 2 O) n ], presenting a metal complex intermediate A and a triethylammonium acetate.…”

Section: Expansion Of the Substrate Scope On The Henry Reactionmentioning

confidence: 91%

Synthesis and Catalytic Application of Two Mononuclear Complexes Bearing Diethylenetriamine Derivative Ligand

et al. 2020

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Two mononuclear zero-dimensional Ni(II) and Zn(II) complexes bearing diethylenetriamine derivative ligand, namely [NiL(CH3COO)2(H2O)] (1) and [ZnL(CH3COO)2] (2) [L = N, N’-bis(2-hydroxybenzyl)diethylenetriamine], were synthesized under reflux conditions. The molecular composition and structure of the complexes were identified by IR, PXRD, elemental analyses, and single crystal X-ray diffraction. Complex 1 belongs to a monoclinic crystal system with the P21/n space group, and Complex 2 belongs to a monoclinic crystal system with the C2/c space group. The Henry reaction of nitromethane with aromatic aldehydes was explored with Complexes 1 and 2 as the catalyst. Results from the catalytic reaction revealed that the complexes displayed excellent catalytic activities under the optimized conditions and that the substrate scope of aromatic aldehydes could be extended to a certain extent. In addition, the possible catalytic mechanism of the Henry reaction was also deduced.

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Section: Expansion Of the Substrate Scope On The Henry Reactionmentioning

confidence: 91%

Synthesis and Catalytic Application of Two Mononuclear Complexes Bearing Diethylenetriamine Derivative Ligand

et al. 2020

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“…[103] Zhou developed the first asymmetric form of the Henry reaction by using the Cu-Schiff base complex to resolve these drawbacks. [104] In 2011, Ozturk [105] synthesized a chiral complex of Schiff base ligand 127 based on ferrocene under microwave treatment and solvent-free green chemistry approaches (Scheme 30). They found that the ferrocene carbaldehyde 125 readily responded with the different chiral amines 126 and amino alcohols in ethanol solvent in the presence of copper triflate (source of metal ion) to provide chiral Schiff base 127 (Scheme 31) in 40 h in the presence of CH 2 Cl 2 , thus, giving enantioselectivity of about 95 % ee.…”

Section: Chemistryselectmentioning

confidence: 99%

Recent Advances in the Catalytic Applications of Chiral Schiff‐Base Ligands and Metal Complexes in Asymmetric Organic Transformations

Jain

Barman

2022

ChemistrySelect

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The Schiff base and its metal complexes are extensively studied for their adaptable metal chelating properties. Their ability to alter the design and modify it for various organic and biological applications makes them versatile compounds. The chiral Schiff base and their metal complexes possess excellent stability in very high temperatures, making them a suitable candidate for organocatalysts in reactions involving harsh conditions. Besides, these chiral complexes of Schiff base can transform their chirality in the final product formed in different chemical reactions. This stereo-induction by the chiral metal complexes of Schiff base is considerably valuable for synthesizing high optically active compounds in the field of medicinal and natural product synthesis. Thus, this review emphasizes the latest and relevant literature concerning the asymmetric catalysis of chiral Schiff base ligand-metal complexes in various synthetic organic transformation reactions. The synthesis and the catalytic mechanisms of various reactions are discussed, including their enantioselectivities, diastereoselectivities, regioselectivities, and stereoselectivities of different complexes to organic transformation.

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In3+ doped magnesium ferrite an efficient magnetic catalyst for the synthesis of functionalized quinazolinone and Henry reaction

Naik¹,

Rodrigues

Torney

et al. 2022

J Chem Sci

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Asymmetric Henry reaction catalyzed by Cu(I)-based chiral amino alcohol complex

Cited by 4 publications

References 17 publications

Synthesis and Catalytic Application of Two Mononuclear Complexes Bearing Diethylenetriamine Derivative Ligand

Synthesis and Catalytic Application of Two Mononuclear Complexes Bearing Diethylenetriamine Derivative Ligand

Recent Advances in the Catalytic Applications of Chiral Schiff‐Base Ligands and Metal Complexes in Asymmetric Organic Transformations

In3+ doped magnesium ferrite an efficient magnetic catalyst for the synthesis of functionalized quinazolinone and Henry reaction

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