An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones

Huo, Xiaohong; He, Rui; Zhang, Xiǎo; Zhang, Wanbin

doi:10.1021/jacs.6b06156

Cited by 324 publications

(108 citation statements)

References 60 publications

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“…Recently, Zhang developed an Ir/Zn bimetallic dual catalytic system for the diastereodivergent enantioselective α‐allylation of unprotected α‐hydroxyketones (Scheme ) . Still, the reactive allyliridium intermediate generated in the presence of the phosphoramidite derivative 27 /iridium complex and allylic esters.…”

Section: Diastereodivergency By Two Chiral Catalystsmentioning

confidence: 99%

Catalytic Strategies for Diastereodivergent Synthesis

Lin

Feng

2017

Chemistry A European J

228

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Chiral molecules with multiple stereocenters are widely distributed in nature and drugs. Asymmeric catalysis has allowed the formation of a chiral molecule's enantiomers with equal ease by applying the enantiomeric pair of a chiral catalyst. However, the diastereodivergent synthesis is a great challenge because the formation of one of the diastereomers is inherently preferred in most reactions. Under the efforts of chemists, elegant strategies have been developed to full control of absolute and relative stereochemical configurations. In this Minireview, we highlight the significant advances achieved in this field, and present the diastereo-control mechanism in the appropriate place on the expectation that new diastereodivergent strategies can be inspired and more types of enantioselective diastereodivergent reactions can be realized.

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Section: Diastereodivergency By Two Chiral Catalystsmentioning

confidence: 99%

Catalytic Strategies for Diastereodivergent Synthesis

Lin

Feng

2017

Chemistry A European J

228

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“…3 Zhang and co-workers reported the combination of iridium and zinc catalysts for the related allylation of α -hydroxy phenones. 4 An approach to the stereodivergent allylation of carbonyl compounds in the carboxylic acid oxidation state has not been published. 5 …”

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confidence: 99%

Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis

2016

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The preparation of all possible stereo-isomers of a given chiral molecule bearing multiple stereocenters by a simple and unified method is a significant challenge in asymmetric catalysis. We report stereodivergent allylic substitutions with aryl acetic acid esters catalyzed synergistically by a metallacyclic iridium complex and benzotetramisole. Through permutations of the enantiomers of the two chiral catalysts, all four stereoisomers of the products bearing two adjacent stereocenters are accessible with high diastereoselectivity and enantioselectivity. The resulting chiral activated ester products can be converted readily to enantioenriched amides, unactivated esters, and carboxylic acids in a one-pot manner.

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“…[37] So gelang die a-Allylierung von nicht geschützten a-Hydroxyketonen durch die kombinierte Wirkung eines chiralen Ir-Phosphoramiditkomplexes und eines chiralen Zn-ProPhenol-Komplexes (Schema 16). [37] So gelang die a-Allylierung von nicht geschützten a-Hydroxyketonen durch die kombinierte Wirkung eines chiralen Ir-Phosphoramiditkomplexes und eines chiralen Zn-ProPhenol-Komplexes (Schema 16).…”

Section: Metallkatalytische Methodenunclassified

Direkte asymmetrische Alkylierung von Ketonen: noch immer ein unerreichtes Ziel

2017

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Die Alkylierung von Ketonen ist Teil des Grundstudiums der Chemie. In vielen Fällen führt diese Umwandlung zu einem neuen stereogenen Zentrum. Allerdings täuscht die scheinbare Einfachheit der Umwandlung über eine Reihe von Schwierigkeiten hinweg, die so groß sind, dass eine allgemeine Methode für die direkte asymmetrische Alkylierung von Ketonen bisher unerreicht ist. Trotz der Weiterentwicklung der Organo‐ und Übergangsmetallkatalyse liefert bisher keine von beiden eine adäquate Lösung. Sogar die Anwendung eines effizienten und allgemein verwendbaren stöchiometrischen Reagens muss erst noch beschrieben werden. Dieser Kurzaufsatz beschreibt den aktuellen Stand in Bezug auf direkte Alkylierungsreaktionen einiger Carbonylgruppen und bespricht den begrenzten Fortschritt bei Ketonen sowie mögliche Wege, die letztlich zu einer breit anwendbaren Methode für die asymmetrische Alkylierung von Ketonen führen können.

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An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones

Cited by 324 publications

References 60 publications

Catalytic Strategies for Diastereodivergent Synthesis

Catalytic Strategies for Diastereodivergent Synthesis

Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis

Direkte asymmetrische Alkylierung von Ketonen: noch immer ein unerreichtes Ziel

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