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WIREs Comput Mol Sci
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Organocatalysis: Cinchona catalysts

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The resurgence of asymmetric organocatalysis has been accompanied by the development of countless synthetic methodologies making use of Cinchona alkaloids (or their derivatives) as catalysts. Although important steps have been made in the understanding of the mode of action of this class of compounds, the development of new catalytic methodologies is largely carried out using experiment‐driven approaches. This overview presents a selection of computational results on the behavior of Cinchona alkaloids with respect to their structure, the way they interact with other species, and, ultimately, their catalytic activity. The twofold aim of this contribution is to provide organic chemists with accessible information on computational results as well as to present theoretical chemists an overview of the methods commonly used to model Cinchona organocatalysts, and how they are comparable to experimental results. © 2011 John Wiley & Sons, Ltd. WIREs Comput Mol Sci 2011 1 142–152 DOI: 10.1002/wcms.2

Figure 1.

The structure of Cinchona alkaloids.

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Figure 2.

Main stable conformations of Cinchona alkaloids.

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Figure 3.

Model chromatographic selectors, chiral analytes, and representative interactions.

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Figure 4.

Surface modifiers, α‐ketoesters employed as substrates in asymmetric heterogeneous hydrogenation and schematic representation of the donor/acceptor interaction between them.

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Figure 5.

A representative asymmetric dihydroxylation ligand and a schematic view of its π interactions with an aromatic substrate.

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Figure 6.

R3N+CH···X interactions in the complex between a nitronate, an N‐carbamoyl imine, and a model ammonium catalyst.

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Figure 7.

An epi‐C9‐thiourea catalyst and a schematic representation of its (experimentally observed) solution dimer.

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Figure 8.

Bifunctional catalysis in the asymmetric addition of β‐ketoesters to N‐phenyl maleimide.

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Figure 9.

Asymmetric intramolecular cyclopropanation using a C2′‐methylated Cinchona derivative.

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Figure 10.

Asymmetric (formal) [1,3]‐sigmatropic rearrangement of allyl trichloroacetimidates.

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Figure 11.

Mechanistic duality in tertiary amine/thiourea organocatalysis exemplified for a conjugate addition. EWG, electron withdrawing group.

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Electronic Structure Theory > Density Functional Theory
Theoretical and Physical Chemistry > Reaction Dynamics and Kinetics
Structure and Mechanism > Molecular Structures
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