Chapter 6 Cinchona Alkaloids

Verpoorte, Robert; Schripsema, Jan; Leer, T. van der

doi:10.1016/s0099-9598(08)60231-x

Cited by 11 publications

(5 citation statements)

References 177 publications

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“…Historically, the cinchona alkaloids were the first chiral amines to be used in asymmetric catalysis, most notably in the pioneering work of Pracejus from the 1960s on disubstituted ketene alcoholysis. Cinchona alkaloids also possess a rich and colorful history that is rooted in natural products and pharmaceutical chemistry . They are isolated en masse by extracting the bark of the cinchona tree, which is native to tropical regions.…”

Section: Introduction and Historical Perspectivementioning

confidence: 99%

Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis

2003

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Section: Introduction and Historical Perspectivementioning

confidence: 99%

Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis

2003

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“…The quinuclidine nucleus is the bridged bicyclic core of naturally occurring cinchona alkaloids [39]. The quinuclidine derivatives might be elaborated through the bridging annulation of β-enamino ester (S)-27 via asymmetric Michael-type cyclization, prepared from β-keto ester (E)-25b.…”

Section: Methods Of Constructing Quinuclidine Systemsmentioning

confidence: 99%

Chemistry of quinuclidines as nitrogen bicyclic bridged‐ring structures

Hamama

El-Magid

Zoorob

2006

Journal of Heterocyclic Chem

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“…Studies on the difference in biological activity of natural Cinchona alkaloids with respect to their structural, stereochemical and physicochemical properties have attracted much attention owing to the pharmacological interest in these compounds (Verpoorte et al, 1988). Recently, Cinchona alkaloids and their derivatives have been investigated as natural organocatalysts giving asymmetric induction in organic reactions with the formation of stereogenic centres (Song, 2009).…”

Section: Commentmentioning

confidence: 99%

Tosyl esters of cinchonidine and cinchonine alkaloids: the structure–reactivity relationship in the hydrolysis to 9-epibases

Karczmarzyk¹,

Lipińska²,

Wysocki³

et al. 2011

Acta Crystallogr C

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In the crystal structures of the diastereoisomers of O-tosylcinchonidine [(9R)-cinchon-9-yl 4-methylbenzenesulfonate], (I), and O-tosylcinchonine [(9S)-cinchon-9-yl 4-methylbenzenesulfonate], (II), both C(26)H(28)N(2)O(3)S, both molecules are in an anti-closed conformation and, in each case, the position of the aryl ring of the tosylate system is influenced by an intramolecular C-H···O hydrogen bond. The molecular packing in (I) is influenced by weak intermolecular C-H···O and C-H···π interactions. The crystal structure of (II) features C-H···π interactions and van der Waals forces only. The computational investigations using RHF/6-31G** ab initio and AM1 semi-empirical methods performed for (I) and (II) and their protonated species show that the conformational and energetic parameters of the molecules are correlated with differences in their reactivity in hydrolysis to the corresponding 9-epibases.

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Chapter 6 Cinchona Alkaloids

Cited by 11 publications

References 177 publications

Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis

Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis

Chemistry of quinuclidines as nitrogen bicyclic bridged‐ring structures

Tosyl esters of cinchonidine and cinchonine alkaloids: the structure–reactivity relationship in the hydrolysis to 9-epibases

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