Polymer-supported chiral α-amino amides for the asymmetric addition of diethylzinc to aldehydes: Transforming an inactive homogeneous system into an efficient catalyst

Escorihuela, Jorge; González, Laura; Altava, Belén; Burguete, M. Isabel; Luis, Santiago V.

doi:10.1016/j.apcata.2013.04.030

Cited by 17 publications

(10 citation statements)

References 61 publications

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“…20 The conversion of the aminomethyl resins into amino amide functionalized polymers was carried out by reaction with N-Cbz-(S)-phenylalanine succinimide ester and nal deprotection of the amine groups with 33% HBr/HOAc treatment, following a similar protocol to that used for the preparation of related compounds in solution. 14,15,21 The nal functionalized resins showed the complete absence of the Cbz band at 1716 cm À1 in their IR spectra.…”

Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

“…Taking into consideration our previous results showing the excellent reactivity and enantioselectivity obtained in the addition of organozinc reagents to aldehydes displayed by polymersupported chiral amino amides (2), 14 as well as the ability of the Ni(II) complexes of homogeneous amides 1 to achieve a dual stereocontrol for this reaction through different metal : ligand stoichiometries, 15 we envisaged the potential of the related nickel complexes as green catalyst systems for the addition of organozinc reagents to aldehydes with efficient dual stereocontrol. In this regard, the approach shown in Scheme 1 was considered for the preparation of the corresponding supported Ni(II) complexes with 1 : 1 and 1 : 2 stoichiometries.…”

Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

“…15 General procedure for the preparation of nickel complexes with 1 : 1 metal : ligand stoichiometry (3)…”

Section: Synthesis Of Resinsmentioning

confidence: 99%

“…2). 15 In the past years, the possibility of obtaining both enantiomers using a single chiral source by changing the reaction conditions has received special attention. 16 This dual stereocontrol can be achieved in different ways, such as using different metals coordinated to the chiral ligand, by modication of the solvent system or by introducing structural features that modify the catalytic mechanism or the structure of the catalytic site.…”

Section: Introductionmentioning

confidence: 99%

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Dual stereocontrolled alkylation of aldehydes with polystyrene-supported nickel complexes derived from α-amino amides

et al. 2015

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Nickel(II) complexes derived from a-amino amide ligands anchored to gel-type and monolithic polymers act as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes. Similar to the analogous homogeneous systems, dual stereocontrol in addition products can be achieved by controlling the stoichiometry of the immobilized nickel complex. Aromatic and aliphatic aldehydes were alkylated in good yields with enantioselectivities comparable to those obtained with the homogeneous analogues. These polymer-supported catalysts offer significant advantages as no metal leaching is observed and they can be easily recovered from the reaction mixture by simple filtration and reused for subsequent experiments with consistent catalytic activity.

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Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

Section: Catalyst Preparation and Characterizationmentioning

confidence: 99%

“…15 General procedure for the preparation of nickel complexes with 1 : 1 metal : ligand stoichiometry (3)…”

Section: Synthesis Of Resinsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Dual stereocontrolled alkylation of aldehydes with polystyrene-supported nickel complexes derived from α-amino amides

et al. 2015

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“…because they are inert, nontoxic, nonvolatile, insoluble and recyclable [15], [16]. Among the polymeric supports, chloromethylated polystyrene crosslinked with divinylbenzene is one of the most widely used supports [17].…”

Section: Introductionmentioning

confidence: 99%

Polymer Supported Schiff Base Iron Complex for Epoxidation of Trans-stilbene

Nath¹,

Pradhan²,

Maharana³

et al. 2017

IJCEA

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Abstract-In the present investigation, the novel recyclable polystyrene anchored iron complex supported by -ONN Schiff base is synthesized. This polymer anchored iron complex is prepared by the reactions of metal solution with one molar equivalent of polystrene supported Schiff-base ligands in methanol under nitrogen atmosphere. In contrast with other polymer-supported catalysts, the greatest advantage of this catalyst system was that the cost of the catalyst was remarkably low and recycled up to six times, due to the easily accessible materials and the simple synthetic route. The higher efficiency of complexation of metal ions on the polymer anchored Schiff base than unsupported analogue was another advantages of this catalyst system. The structural study reveal that iron(III) complex is octahedral in geometry.The catalytic activities of polystyrene supported iron complex toward the epoxidation of trans-Stilbene is investigated. Experimental results indicate that the reactivity of iron complex is dramatically affected by the polymer support and the rate of trans-Stilbene conversion was 4.27 × 10 -7 moledm -3 s -1 and obeys first order kinetics. The efficiency of supported catalysts remained almost constant upto six recycles.

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Chiral Room Temperature Ionic Liquids as Enantioselective Promoters for the Asymmetric Aldol Reaction

et al. 2014

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Polymer-supported chiral α-amino amides for the asymmetric addition of diethylzinc to aldehydes: Transforming an inactive homogeneous system into an efficient catalyst

Cited by 17 publications

References 61 publications

Dual stereocontrolled alkylation of aldehydes with polystyrene-supported nickel complexes derived from α-amino amides

Dual stereocontrolled alkylation of aldehydes with polystyrene-supported nickel complexes derived from α-amino amides

Polymer Supported Schiff Base Iron Complex for Epoxidation of Trans-stilbene

Chiral Room Temperature Ionic Liquids as Enantioselective Promoters for the Asymmetric Aldol Reaction

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