Asymmetric Magnesium‐Catalyzed Hydroboration by Metal‐Ligand Cooperative Catalysis

Falconnet, Alban; Magre, Marc; Maity, Bholanath; Cavallo, Luigi; Rueping, Magnus

doi:10.1002/ange.201908012

Cited by 7 publications

(3 citation statements)

References 63 publications

(6 reference statements)

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“…Rueping and his research group provided an alternative simple and innovative methodology for the enantioselective synthesis of alcohols by the reduction of carbonyl compounds by commercially available chiral magnesium complex. [ 59 ] Excellent yields and enantioselectivities for a variety of ketones undergoing MgBu 2 ‐catalyzed asymmetric hydroboration in the presence of HBpin and chiral ( R )‐(+)‐BINOL ligand were obtained. Computational studies established that the reaction proceeds via the formation of magnesium‐ligand cooperativity and the BINOL ligand act as a non‐innocent ligand.…”

Section: Magnesium‐catalyzed Reduction Of Unsaturated Substratesmentioning

confidence: 99%

Recent developments in the reduction of unsaturated bonds by magnesium precursors

Banerjee

Panda

2021

Applied Organom Chemis

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Scientists have witnessed significant breakthroughs in s‐block metal chemistry. Over the past few years, several applications in catalysis associated with alkaline‐earth metal catalysts have been established owing to their abundance and lower cost. These catalysts have proved to be essential alternatives to transition metal catalysts. Several research groups have recognized the importance of magnesium complexes as highly active metal catalysts in the reduction of a series of unsaturated substrates for the synthesis of ubiquitous compounds necessary for industrial purposes. This minireview presents, based on studies published in the past recent years, a detailed discussion of catalytic hydroelementation on C–X (X = C, N, O, B, Si, S) multiple bonds, promoted by novel magnesium metal catalysts.

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Section: Magnesium‐catalyzed Reduction Of Unsaturated Substratesmentioning

confidence: 99%

Recent developments in the reduction of unsaturated bonds by magnesium precursors

Banerjee

Panda

2021

Applied Organom Chemis

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“…9 Using various chiral ligands, asymmetric hydrogenation of α,β-unsaturated ketones to saturated ketones and unsaturated allylic alcohols with high enantioselectivity has recently been performed. [10][11][12] However, to eliminate water and oxygen, which poses some functional problems, the hydrogenation reactions are typically carried out under the inert environment. These methods suffer from many disadvantages, such as environmental toxicity, strong requirements for chemical reduction, unsatisfactory enantioselectivity, and low yield.…”

Section: Introductionmentioning

confidence: 99%

Regioselective asymmetric bioreduction of trans‐4‐phenylbut‐3‐en‐2‐one by whole‐cell of Weissella cibaria N9 biocatalyst

Kalay

Şahin

2021

Chirality

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There is a considerable interest in the asymmetric production of chiral allylic alcohols, the main building blocks of many functional molecules. The asymmetric reduction of α,β-unsaturated ketones is difficult with traditional chemical protocols in a regioselective and stereoselective manner. In this study, the reductive capacity of whole cell of Leuconostoc mesenteroides N6, Weissella paramesenteroides N7, Weissella cibaria N9, and Leuconostoc pseudomesenteroides N13 was investigated as whole-cell biocatalysts in the enantioselective reduction of (E)-4-phenylbut-3-en-2-one (1). The biocatalytic reduction of 1 to (S,E)-4-phenylbut-3-en-2-ol ((S,E)-2) using the whole cell of W. cibaria N9 isolated from Turkish sourdough was developed in a regioselective fashion, occurring with excellent conversion and recovering the product in good yield. In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. In addition, to our knowledge, this is the first report on production of (S,E)-2 using whole-cell biocatalyst in excellent yield, conversion with enantiopure form and at gram scale. These findings pave the way for the use of whole cell of W. cibaria N9 for challenging higher substrate concentrations of different α,β-unsaturated ketones for regioselective reduction at industrial scale.

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“…In these, the symmetric cyclohexadienones could be efficiently obtained by oxidation and olefin metathesis reactions using simple substituted phenols (Figure ). Bifunctional magnesium catalysts are selected to mediate the current desymmetrization reaction, for which magnesium is widely distributed in nature, present a wide range of low toxicity, and represent an attractive catalyst source.…”

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confidence: 99%

Desymmetrization Process by Mg(II)-Catalyzed Intramolecular Vinylogous Michael Reaction

Yang

Peng

et al. 2020

Org. Lett.

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Chiral magnesium catalyzed intramolecular vinylogous Michael reaction of novel cyclohexadienones via a desymmetrization process is reported. (R)-BINOL derived ligand and an achiral amide were employed in the current in situ generated magnesium catalyst, giving the corresponding hydrogenated benzofuranone skeletons in good to excellent enantioselectivities with high yields. This simple and efficient strategy could be utilized for the synthesis of aromatized α,β-unsaturated ester and Br-substituted hydrogenated benzofuranone in good yields under mild conditions. Letter pubs.acs.org/OrgLett

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Asymmetric Magnesium‐Catalyzed Hydroboration by Metal‐Ligand Cooperative Catalysis

Cited by 7 publications

References 63 publications

Recent developments in the reduction of unsaturated bonds by magnesium precursors

Recent developments in the reduction of unsaturated bonds by magnesium precursors

Regioselective asymmetric bioreduction of trans‐4‐phenylbut‐3‐en‐2‐one by whole‐cell of Weissella cibaria N9 biocatalyst

Desymmetrization Process by Mg(II)-Catalyzed Intramolecular Vinylogous Michael Reaction

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