Iminium Catalysis

Erkkilä, A.; Majander, Inkeri; Pihko, Petri M.

doi:10.1021/cr068388p

Cited by 1,386 publications

(535 citation statements)

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“…44 Both activation modes have been elegantly combined in asymmetric domino reactions, which now constitute possibly one of the most applied one-pot multistep approaches in organocatalysis. 7,44e This strategy is outlined in Fig.…”

Section: Secondary Amine Catalystsmentioning

confidence: 99%

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

2012

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The evolution of organocatalysis led to various valuable approaches, such as multicomponent as well as domino and tandem reactions. Recently, organomulticatalysis, i.e., the modular combination of distinct organocatalysts enabling consecutive reactions to be performed in one pot, has become a powerful tool in organic synthesis. It allows the construction of complex molecules from simple and readily available starting materials, thereby maximizing reaction efficiency and sustainability. A logical extension of conventional multicatalysis is a multicatalyst, i.e., a catalyst backbone equipped with independent, orthogonally reactive catalytic moieties. Herein we highlight the impressive advantages of asymmetric organomulticatalysis, examine its development, and present detailed reactions based on the catalyst classes employed, ranging from the very beginnings to the latest multicatalyst systems. R. C. Wende was born inRosenberg (Olesno), Poland, in 1984. He studied chemistry at the Justus-Liebig University, Giessen, where he obtained his B. Sc. degree in 2008 and his M. Sc. degree in 2010. Currently he is working on his PhD under the supervision of P. R. Schreiner. His research focuses on the development of novel synthetic oligopeptide and thiourea organocatalysts for multicatalysis reactions.

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Section: Secondary Amine Catalystsmentioning

confidence: 99%

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

2012

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“…10−13 However, organocatalytic activation of typically inert β -carbon of saturated carbonyl compounds remains one of the most difficult challenges for organic chemists (Scheme 1c). Direct β -carbon functionalization of carbonyls has generally been confined to the addition of nucleophiles to α ,β -unsaturated carbonyl compounds such as via iminium catalysis 14 and the Nheterocyclic carbene (NHC)-induced Umpolung reactivity of α ,β -unsaturated carbonyl compounds that allows β -carbon functionalization with another carbonyl compounds. 15 Several new trends are being introduced for direct β -functionalization of carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

Achieving elusive transformations with organocatalysis: direct $\beta $-carbon activation of saturated carbonyl compounds

Shaikh¹

2017

Turk J Chem

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Direct β -carbon activation of saturated carbonyl compounds for carrying out fast forward β -functionalization has been one of the most difficult to achieve tasks in catalysis. In the past few years, this challenging issue has attracted considerable attention among the chemical community that has led to fruitful developments to accomplish this elusive transformation. In this short review, we highlight recent developments for direct β -carbon functionalization of saturated carbonyl compounds based on conceptually new methods including oxidative enamine catalysis, N -heterocyclic carbene (NHC)-assisted catalysis, and photoredox catalysis.

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“…3 This is due, in part, to the wide variety of reactions which have been developed using secondary amines along with the excellent yields and outstanding levels of selectivity which are commonly achieved in these transformations. 4,5 The field also follows some of the principles of Green chemistry which has further enhanced applicability, particularly in the industrial environment. Reducing levels of catalyst loading necessary to bring about reaction at an effective rate would further increase this potential.…”

Section: Introductionmentioning

confidence: 99%

Improving catalyst activity in secondary amine catalysed transformations

et al. 2015

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This version is available at https://strathprints.strath.ac.uk/56149/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of L-phenylalanine N-methyl amide with acetophenone derivatives results in a series of imidazolidinones whose salts can be used to accelerate the Diels-Alder cycloaddition. Electron withdrawing groups significantly increases the overall rate of cycloaddition without compromise in selectivity. The most effective catalyst was shown to be efficient for a variety of substrates and the applicability of this catalyst to alternative secondary amine catalysed transformations is also discussed.

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Iminium Catalysis

Cited by 1,386 publications

References 304 publications

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

Evolution of asymmetric organocatalysis: multi- and retrocatalysis

Achieving elusive transformations with organocatalysis: direct $\beta $-carbon activation of saturated carbonyl compounds

Improving catalyst activity in secondary amine catalysed transformations

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