Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles

Ohmatsu, Kohsuke; Kiyokawa, Mari; Ooi, Takashi

doi:10.1021/ja1102844

Cited by 182 publications

(79 citation statements)

References 36 publications

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“…Ooi and co-workers have reported the development of chiral 1,2,3-triazolium salts (such as 152ÁBr) that function as cationic organocatalysts with anion recognition abilities. 84 The increased CH-acidity of the triazolium cation versus the simple 1,4-disubstituted 1,2,3-triazole unit means an increased anion binding capacity. X-ray crystallography of 152ÁCl showed that the combination of electrostatic interactions, CHÁ Á Áanion hydrogen bonding and a suitably positioned amide NHÁ Á Áanion hydrogen bond forms a structured and tightly bound ion pair.…”

Section: Catalysismentioning

confidence: 99%

Anion receptor chemistry: highlights from 2008 and 2009

2010

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Section: Catalysismentioning

confidence: 99%

Anion receptor chemistry: highlights from 2008 and 2009

2010

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“…18 The catalyst ability of 22 was initially examined in asymmetric phase-transfer alkylation of oxindole derivative 24a. 13 Although newly-designed catalyst 22a…”

Section: Amino Acid-derived Catalystsmentioning

confidence: 99%

A new generation of chiral phase-transfer catalysts

2016

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Phase-transfer catalysis has long been recognized as a versatile method for organic synthesis. In particular, during more than the past three decades, asymmetric phase-transfer catalysis based on the use of structurally well-defined chiral catalysts has become a topic of great scientific interest. Although various effective chiral catalysts have already been reported and these catalysts were utilized for practical asymmetric transformations, further design and development of new chiral phase-transfer catalysts are still attractive research subjects in organic chemistry due to the high utility and practicability of phase-transfer-catalyzed reactions. This review focuses on the recent examples of newly designed effective chiral phase-transfer catalysts.

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“…Die Optimierung der Katalysatorstruktur und des Lçsungs-mittels führte zu nahezu quantitativen Ausbeuten und Enantiomerenüberschüssen bis 97 %. [226] 6.1.2. Chirale Anionen als Katalysatoren in der organischen Chemie…”

Section: Anionenkanäleunclassified

Supramolekulare Chemie von Anionen: von der Erkennung zur chemischen Anwendung

Evans

Beer

2014

Angewandte Chemie

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Seit der Jahrtausendwende fanden bemerkenswerte Fortschritte bei der Bindung und dem Nachweis von Anionen statt, die teilweise von den Erkenntnissen zur Ausnutzung von Wasserstoffbrücken ebenso wie den zuvor selten eingesetzten Anionen‐π‐Wechselwirkungen und Halogenbrücken angetrieben wurden. Die supramolekulare Chemie von Anionen wurde indes substantiell über die Anionenerkennung hinaus weiterentwickelt und umfasst nun verschiedene Disziplinen. Große Fortschritte wurden bei der Synthese von Makrocyclen und ineinandergreifenden molekularen Architekturen mit Anionen als Templaten erzielt, während die Untersuchung von anionischen Transmembrantransportern aus dem Nichts heraus zu einem rasch wachsenden Forschungsgebiet erblühte. Die supramolekulare Chemie der Anionen kam außerdem in verschiedenen Anwendungsbereichen wie der Katalyse, der Ionenextraktion und der Verwendung von Anionen als Impuls für molekulare Systeme zum praktischen Einsatz.

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Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles

Abstract: Chiral 1,2,3-triazoliums have been designed, and the rational structural modification based on their unique anion-binding abilities has led to the establishment of the highly enantioselective alkylation of 3-substituted oxindoles.

Cited by 182 publications

References 36 publications

Anion receptor chemistry: highlights from 2008 and 2009

Anion receptor chemistry: highlights from 2008 and 2009

A new generation of chiral phase-transfer catalysts

Supramolekulare Chemie von Anionen: von der Erkennung zur chemischen Anwendung

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