Novel guanidinyl pyrrolidine salt-based bifunctional organocatalysts: application in asymmetric conjugate addition of malonates to enones

Riguet, Emmanuel

doi:10.1016/j.tetlet.2009.05.011

Cited by 25 publications

(4 citation statements)

References 21 publications

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“… − Notably, this very practical synthesis of 5 has been performed previously on kilogram scales in a premanufacturing setting . We confirmed the high enantiomeric purity of 5 (95% ee) by conversion to ketal 6 , , the two diastereomers of which could be readily distinguished by 13 C NMR spectroscopy.…”

Section: Resultssupporting

confidence: 68%

Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane

et al. 2017

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We describe the first systematic study of antimalarial 1,2,4-trioxolanes bearing a substitution pattern regioisomeric to that of arterolane. Conformational analysis suggested that trans-3″-substituted trioxolanes would exhibit Fe(II) reactivity and antiparasitic activity similar to that achieved with canonical cis-4″ substitution. The chiral 3″ analogues were prepared as single stereoisomers and evaluated alongside their 4″ congeners against cultured malaria parasites and in a murine malaria model. As predicted, the trans-3″ analogues exhibited in vitro antiplasmodial activity remarkably similar to that of their cis-4″ comparators. In contrast, efficacy in the Plasmodium berghei mouse model differed dramatically for some of the congeneric pairs. The best of the novel 3″ analogues (e.g., 12i) outperformed arterolane itself, producing cures in mice after a single oral exposure. Overall, this study suggests new avenues for modulating Fe(II) reactivity and the pharmacokinetic and pharmacodynamic properties of 1,2,4-trioxolane antimalarials.

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Section: Resultssupporting

confidence: 68%

Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane

et al. 2017

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“…Riguet made use of a bifunctional pyrrolidine-guanidine catalyst 30 effecting asymmetric Michael addition of malonate derivatives under iminium catalysis (Scheme 16). 39 It was found that the addition of 2 equivalents of pivalic acid favored both the formation of an iminium salt and the deprotonation of the malonate readily complexed by the guanidinium moiety (generated by the second equivalent of pivalic acid) acting as a molecular receptor of malonate. This ion pair in action achieved the enantioselective syn addition of the malonate anion with respect to the pyrrolidine substituent in high ees up to 90%.…”

Section: Counteranion or Cation In Actionmentioning

confidence: 99%

Recent advances in cooperative ion pairing in asymmetric organocatalysis

et al. 2012

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Over the last decade, with the surge in the development of organocatalysis, many processes involving chiral ion pairs have emerged as powerful tools in the design of new efficient organocatalysts. This tutorial review focuses on the recent evolutions of these organocatalytic systems in which both anionic and cationic parts are working in a cooperative fashion in order to develop unique catalytic processes which outperform the existing approaches. In this respect, chiral ion pairs opened new avenues in the design of bifunctional organocatalysts by means of combinatorial approaches.

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“…Novel acyclic catalysts 13 containing guanidine and pyrrolidine moieties developed by Riguet et al. were also utilized in the enantioselective addition of malonates to cyclohexanone . Racemic products were obtained when using free base catalysts 13 , while high enantioselectivities (up to 93 % ee values) were observed after using the corresponding pivalic acid salts of 13 as catalysts.…”

Section: Chiral Guanidines As Asymmetric Catalystsmentioning

confidence: 99%

Recent Advances in Chiral Guanidine‐Catalyzed Enantioselective Reactions

Chou

Leow

Tan

2019

Chemistry An Asian Journal

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Chiral guanidines have been widely used as Brønsted base catalysts and phase transfer catalysts in enantioselectiver eactions. Due to their amendable structure and powerful catalytic ability,t hey have attracted much interest. Several new catalysts containing ag uanidinium moiety have been reported over the past decade and many promising outcomes have been achieved. This article illustrates the progress of chiral guanidine catalysis in asymmetric synthesis from 2009t o2 018. It is an update of ar eview of the same titlepublished in 2009. [4b] [a]

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Novel guanidinyl pyrrolidine salt-based bifunctional organocatalysts: application in asymmetric conjugate addition of malonates to enones

Cited by 25 publications

References 21 publications

Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane

Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane

Recent advances in cooperative ion pairing in asymmetric organocatalysis

Recent Advances in Chiral Guanidine‐Catalyzed Enantioselective Reactions

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