The Ion Tag Strategy as a Route to Highly Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction

Lombardo, Marco; Easwar, Srinivasan; Pasi, Filippo; Trombini, Claudio

doi:10.1002/adsc.200800608

Cited by 103 publications

(38 citation statements)

References 76 publications

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“…They found that catalyst loading could be reduced to 0.1 mol% in the case of electron-poor aromatic aldehydes with ee up to 99%. Under the same reaction conditions, many substrates afforded "enzymatic-like" levels of ees [60]. The recyclability of the catalyst was examined and shown that the product could be readily isolated by extraction using diethyl ether after the excess ketone was removed by vacuum.…”

Section: Scheme 3 Aldol Reaction Catalyzed By An Imidazolium-tagged mentioning

confidence: 99%

Ionic Liquid Immobilized Organocatalysts for Asymmetric Reactions in Aqueous Media

Qiao

Headley

2013

Catalysts

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Ionic liquids are organic salts with melting points typically below ambient or reaction temperature. The unique combination of physical properties of ionic liquids, such as lack of measurable vapor pressure, high thermal and chemical stability, make them ideal to be used as reusable homogenous support for catalysts. In addition, the solubility of ionic liquids in various reaction media can be controlled and easily fine-tuned by modification of the structures of their cations and anions. As a result, ionic liquid immobilized organocatalysts are very effective in aqueous media and can be separated easily from organic solvents, as well as aqueous phases by simply adjusting the polarity of the media. Ionic liquid immobilized organocatalysts are not only very versatile compounds that are effective catalysts for a wide spectrum of reactions, but are also environmentally friendly and recyclable organocatalysts. Herein, we provide a summary of the past decade in the area of asymmetric catalysis in aqueous media for a wide variety of reactions in which ionic liquid and related ammonium salt immobilized organocatalysts are used.

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Section: Scheme 3 Aldol Reaction Catalyzed By An Imidazolium-tagged mentioning

confidence: 99%

Ionic Liquid Immobilized Organocatalysts for Asymmetric Reactions in Aqueous Media

Qiao

Headley

2013

Catalysts

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“…However, lower yields were achieved using aliphatic aldehydes as electrophiles (52-60%), but still excellent diastereo-and enantioselectivities (99% de, 99% ee). Under these conditions, the catalyst was recovered and reused up to five times without deleterious effect in the results [105,106]. Figure 11.…”

Section: Aqueous Aldol Reactions With Supported Organocatalystsmentioning

confidence: 99%

Pursuing Chemical Efficiency by Using Supported Organocatalysts for Asymmetric Reactions under Aqueous Conditions

Guillena

Alonso²,

Baeza³

et al. 2015

COCAT

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Over the past decade, a great effort has been made by the chemical community to improve the efficiency and greenness of reactions. Merging the use of supported and recyclable organocatalysts and aqueous conditions to pursue this goal in the asymmetric synthesis of interesting enantioselective molecules lead to outstanding results in some cases. Progresses in this area also offer the possibility of having even more sustainable processes by implementing these reactions in the large scale production of chiral molecules using automated flow chemistry.

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“…Lombardo 小组 [69,70] 离子对有利于提高催化反应的立体选择性. 因此设计、合成了带离子对的吡咯衍生物 25 (Scheme 9), 催化脂肪醛(正丙醛、正丁醛、正戊醛、异戊醛和异丁醛)与各种取代的硝基乙烯的 Michael 加成放应 [71] .…”

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Progress in the Application of Organocatalysis to Asymmetric Michael Additions

Ying¹,

Wu²,

Fu³

et al. 2012

Chin. J. Org. Chem.

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Organocatalysis has become one of the most intensively research fields. Asymmetric Michael addition is a key method for synthesis of versatile synthetic buildings and pharmaceutical intermediates, which include one or more stereochemical centers. The organocatalysts reported over the past three years for the asymmetric Michael addition are reviewed including primary amine, pyrrolidine based derivatives, (thio) urea, chiral squaramides and phosphoric acids. The relationship between structure of organocatalysts and their catalytic activities, catalytic reaction mechanism and the applications of these protocols for the preparation of drugs and bioactive intermediates are also introduced.

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The Ion Tag Strategy as a Route to Highly Efficient Organocatalysts for the Direct Asymmetric Aldol Reaction

Cited by 103 publications

References 76 publications

Ionic Liquid Immobilized Organocatalysts for Asymmetric Reactions in Aqueous Media

Ionic Liquid Immobilized Organocatalysts for Asymmetric Reactions in Aqueous Media

Pursuing Chemical Efficiency by Using Supported Organocatalysts for Asymmetric Reactions under Aqueous Conditions

Progress in the Application of Organocatalysis to Asymmetric Michael Additions

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