Linear β-amino alcohol catalyst anchored on functionalized magnetite nanoparticles for enantioselective addition of dialkylzinc to aromatic aldehydes

Sappino, Carla; Primitivo, Ludovica; Angelis, Martina De; Righi, Francesco; Pietro, Federica Di; Iannoni, Marika; Pilloni, L.; Ciprioti, Stefano Vecchio; Suber, Lorenza; Ricelli, Alessandra; Righi, Giuliana

doi:10.1039/d0ra04554c

Cited by 8 publications

(13 citation statements)

References 18 publications

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“…In the last years, our group has investigated the catalytic efficiency of β-aminoalcohols and their immobilization on nanomaterials. The new aminoalcohol ligand A was developed, 6 suitably modified to be anchored on superparamagnetic nanoparticle B and employed in the asymmetric catalysis, that is, the addition of organozinc to aldehydes 7 and the addition of nitroalkanes to carbonyl compounds (Henry reaction) 8 ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Core–shell Fe 3 O 4 @SiO 2 nanoparticles 7 were treated with iodopropyltrimethoxysilane in anhydrous toluene, obtaining the iodo-functionalized nanoparticles 1 . Then, the reaction with ephedrine was performed in the presence of DIPEA as a base, leading to the immobilized chiral catalyst 2 .…”

Section: Resultsmentioning

confidence: 99%

“…1 mmol terminal alkyne 4 ( 4a or 4b ) and 1.1 mmol (177 mg) (3-azidopropyl)benzene were treated as reported in ref ( 7 ).…”

Section: Methodsmentioning

confidence: 99%

“…The following compounds were synthetized according to reported procedures: (3-azidopropyl)benzene, silica-coated magnetite nanoparticles (Fe 3 O 4 @SiO 2 ), 5,5-TMS (obtained by end-capping treatment). 7 4.1. General Procedure for the Synthesis of 6.…”

Section: Methodsmentioning

confidence: 99%

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Preparation and Asymmetric Induction Evaluation of the First Ephedrine-Based Ligands Immobilized on Magnetic Nanoparticles

et al. 2021

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Herein, the synthesis and catalytic activity of two ephedrine-based catalysts and two ephedrine-based magnetic nanoparticle-supported catalysts are reported. All catalysts developed were tested in the addition of diethylzinc to aromatic aldehydes and in the Henry reaction. The homogeneous catalysts showed moderate catalytic activity in the organozinc addition and good activity in the Henry reaction, whereas in the case of the nanocatalyst, it was not effective in the addition of diethylzinc to aldehydes and gave reasonable results in the Henry reaction. Moreover, the nanocatalyst remained unchanged over the course of up to three catalytic cycles. To the best of our knowledge, the proposed system is the first recyclable ephedrine-based magnetic nanocatalyst employed in an enantioselective reaction.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…1 mmol terminal alkyne 4 ( 4a or 4b ) and 1.1 mmol (177 mg) (3-azidopropyl)benzene were treated as reported in ref ( 7 ).…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Preparation and Asymmetric Induction Evaluation of the First Ephedrine-Based Ligands Immobilized on Magnetic Nanoparticles

et al. 2021

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“…In 2020, the same authors described the synthesis of a chiral linear 1,2-amino alcohol catalyst 102 anchored on functionalized magnetite nanoparticles which was further investigated in the same reactions [60]. As illustrated in Scheme 33, ZnEt 2 was added to aromatic aldehydes 47 in toluene at room temperature by using 6 mol% of this heterogeneous catalyst, thus providing the corresponding chiral alcohols 100 in moderate yields (46-77%) and enantioselectivities (47-58% ee).…”

Section: Addition To Aldehydesmentioning

confidence: 99%

Recent developments in enantioselective zinc-catalyzed transformations

Pellissier

2021

Coordination Chemistry Reviews

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This review collects the recent advances in the field of enantioselective zinc-catalyzed transformations, covering the literature since the beginning of 2015, illustrating the power of chiral green zinc catalysts to promote all types of reactions. A range of highly enantioselective reactions have been developed in the last six years, including cycloadditions, alkynylation/allylation reactions of carbonyl compounds and derivatives, additions of diorganozincs to carbonyl compounds and derivatives, Mannich reactions, (nitro)aldol reactions, other 1,2-nucleophilic additions to carbonyl compounds and derivatives, Michael additions, Friedel-Crafts reactions, reductions, a-functionalizations of carbonyl compounds, ringopening reactions, epoxidations, halolactonizations, domino/tandem reactions and miscellaneous reactions.

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A C3‐Symmetric Amino Organocatalyst for Asymmetric Synthesis of Warfarin and Analogues: Mechanistic Insight from ESI‐MS Spectrometry and Computational Calculations

Sorato,

De Angelis,

Badasa Oljira

et al. 2024

ChemCatChem

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A novel C3‐symmetric multi‐amino catalyst was synthesized and evaluated in the asymmetric Michael addition to produce warfarin and its analogues. The multi‐amino catalyst turned out to be efficient up to 1% molar without the use of acidic additives providing the desired product in 82% yield and maintaining good level of enantioselectivity. ESI‐MS experiments together with data supplied by theoretical models allowed us the understand the operating mechanism of the catalyst, clarifying the role of the amine functions and confirming the catalyst’s multifunctionality. The presence of three active catalytic sites makes it easy its anchoring to silica as solid support for applications in heterogeneous phase catalysis.

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Linear β-amino alcohol catalyst anchored on functionalized magnetite nanoparticles for enantioselective addition of dialkylzinc to aromatic aldehydes

Abstract: The catalytic activity of a linear β-amino alcohol ligand anchored on functionalized magnetite/silica core–shell nanoparticles has been evaluated in the addition of dialkylzinc to aldehydes leading to promising results.

Cited by 8 publications

References 18 publications

Preparation and Asymmetric Induction Evaluation of the First Ephedrine-Based Ligands Immobilized on Magnetic Nanoparticles

Preparation and Asymmetric Induction Evaluation of the First Ephedrine-Based Ligands Immobilized on Magnetic Nanoparticles

Recent developments in enantioselective zinc-catalyzed transformations

A C3‐Symmetric Amino Organocatalyst for Asymmetric Synthesis of Warfarin and Analogues: Mechanistic Insight from ESI‐MS Spectrometry and Computational Calculations

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