Highly Enantioselective Aza‐Baylis–Hillman Reaction in a Chiral Reaction Medium

Gausepohl, Rolf; Buskens, Pascal; Kleinen, Jochen; Bruckmann, Angelika; Lehmann, Christian W.; Klankermayer, Jürgen; Leitner, Walter

doi:10.1002/anie.200600327

Cited by 170 publications

(73 citation statements)

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“…The first example of an ionic liquid with a chiral anion was reported in 1999 by Seddon et al in a study dealing with lactate ionic liquids. [1] Further ionic liquids with chiral anions were prepared later by the groups of Ohno, [2] Machado, [3] and Leitner [4] derived from 19 natural amino acids, (S)-10-camphorsulfonate and (R)-1,10-binaphthylphosphate, and borate anions based on l-(À)-malic acid, respectively. Chiral cations are also accessible from the chiral pool; however, usually multistep syntheses are necessary.…”

mentioning

confidence: 99%

Effective Chirality Transfer in Ionic Liquids through Ion‐Pairing Effects

et al. 2007

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mentioning

confidence: 99%

Effective Chirality Transfer in Ionic Liquids through Ion‐Pairing Effects

et al. 2007

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“…While malic and tartaric acids have already been reported as anions of some chiral ionic liquids, [23][24][25] the use of (S)-malic acid for the synthesis of chiral ionic liquids based on a chiral cation is unprecedented, to the best of our knowledge.…”

Section: N Bn Bnmentioning

confidence: 98%

Synthesis of novel enantiopure ionic liquids from (S)-malic acid

Bonanni¹,

Manuelli²,

Goti³

et al. 2013

Arkivoc

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“…It is even possible to incorporate the desired functionality directly in the matrix, opening for example new ways of selectivity control. [25] Challenges and Opportunities…”

Section: Organocatalysismentioning

confidence: 99%

Divide et Impera – Multiphase, Green Solvent and Immobilization Strategies for Molecular Catalysis

2006

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The molecular nature of homogeneously dissolved catalysts results -at least in principle -in single-site, well-defined active species for a given catalytic transformation. This favorable situation is common to enzymatic, [1] organometallic, [2] and organo-catalysis, [3] which consequently dominate the area of advanced organic and in particular stereoselective synthesis. The stunning advances in research and applications in these fields over the last thirty years have resulted from the confluence of elegant catalyst design and synthesis, rigorous kinetic and mechanistic investigations, state-of-the-art computational chemistry, and creative use of rapid throughput techniques for generation, testing and analysis. However, in addition to the identification of an appropriate catalyst structure and optimization of reaction conditions for a particular application, the key problem of catalyst separation from products must be addressed within the development of a sustainable commercial process.[4] There are two major drivers for this: First, the costly and often highly specialized catalysts should be recovered and recycled for economic and environmental reasons. Second, the specifications and applications do not allow even trace amounts of catalysts or catalyst components in many products, irrespective of the metallic, organic, or bio-based origin of such impurities.An elegant solution to this problem is the introduction of either a permanent or a temporary phase boundary between the molecular catalyst and the product phase. Typically, the product phase of a molecularly catalyzed reaction will be liquid (often a so-

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Highly Enantioselective Aza‐Baylis–Hillman Reaction in a Chiral Reaction Medium

Cited by 170 publications

References 24 publications

Effective Chirality Transfer in Ionic Liquids through Ion‐Pairing Effects

Effective Chirality Transfer in Ionic Liquids through Ion‐Pairing Effects

Synthesis of novel enantiopure ionic liquids from (S)-malic acid

Divide et Impera – Multiphase, Green Solvent and Immobilization Strategies for Molecular Catalysis

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