Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses

Broeker, Joachim; Knollmueller, M.; Gärtner, Peter

doi:10.1016/j.tetasy.2009.02.004

“…Asymmetric alkylation reactions using polymer-supported chiral auxiliaries have not been widely investigated yet [17]. In this field, solid supported chiral auxiliaries such as Evans'2oxazolidinones [18] and pseudoephedrines [19][20][21][22][23][24][25][26][27][28][29] have been mainly explored. In this research we make modification of poly methylmethacrylate resins which facilitated the synthesis of 2-methyl butanoic acid in a good stereoselectivity.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of optically pure ant pheromones with high enantiomeric purity.

Ai¹,

Mh²,

Aa³

2018

Environ Risk Assess Remediat

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Chemical ecology studies with insects have founded that pheromonal communications often includes several components which can be linear, cyclic or heterocyclic compounds, in the case of chiral pheromones, insect often show the ability to characterize between and respond differently to stereoisomer. Among the most notable are those cases in which differential interspecific responses to enantiomer serve as a species isolating mechanism, the relationship between stereoisomers and pheromone activity are highly specific, meaningful assays and evaluation of the responses of insect to chiral pheromones must be carried out using substances of the highest possible chiral purity, we prepare ant pheromones using poly methyl methacrylate as chiral auxiliaries with high enantiomeric purity and the prepared compounds were characterized with spectroscopic data and the diastereomeric amides were separated using high performance liquid chromatography and give high enantiomeric excess, also we study the biological applications of our products and give agood results.

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meta‐C−H Arylation of Aniline Derivatives via Palladium/ S,O‐Ligand/Norbornene Cooperative Catalysis

Sukowski,

van Borselen,

Mathew

et al. 2023

Angewandte Chemie

2

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Aromatic amines are ubiquitous moieties in organic molecules and their direct functionalization is of great interest in many research areas due to their prevalence in pharmaceuticals and organic electronics. While several synthetic tools exist for the ortho‐ and para‐functionalization of anilines, the functionalization of the less reactive meta‐position is not easy to achieve with current methods. To date, the meta‐C−H arylation of aniline derivatives has been restricted to either the use of directing groups & templates, or their transformation into anilides & quaternary anilinium salts. Herein, we report the first general and efficient meta‐C−H‐arylation of non‐directed aniline derivatives via cooperative catalysis with a palladium–S,O‐ligand–norbornene system. The reaction proceeds under mild conditions with a wide range of aniline derivatives and aryl iodides, while being operationally simple and scalable. Our preliminary mechanistic investigation–including the isolation of several palladium complexes and deuterium experiments–reveal useful insights into the substituent‐effects of both the aniline‐substrate and the norbornene‐mediator during the meta‐C−H activation step.

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meta‐C−H Arylation of Aniline Derivatives via Palladium/ S,O‐Ligand/Norbornene Cooperative Catalysis

Sukowski,

van Borselen,

Mathew

et al. 2023

View full text Add to dashboard Cite

Aromatic amines are ubiquitous moieties in organic molecules and their direct functionalization is of great interest in many research areas due to their prevalence in pharmaceuticals and organic electronics. While several synthetic tools exist for the ortho‐ and para‐functionalization of anilines, the functionalization of the less reactive meta‐position is not easy to achieve with current methods. To date, the meta‐C−H arylation of aniline derivatives has been restricted to either the use of directing groups & templates, or their transformation into anilides & quaternary anilinium salts. Herein, we report the first general and efficient meta‐C−H‐arylation of non‐directed aniline derivatives via cooperative catalysis with a palladium–S,O‐ligand–norbornene system. The reaction proceeds under mild conditions with a wide range of aniline derivatives and aryl iodides, while being operationally simple and scalable. Our preliminary mechanistic investigation–including the isolation of several palladium complexes and deuterium experiments–reveal useful insights into the substituent‐effects of both the aniline‐substrate and the norbornene‐mediator during the meta‐C−H activation step.

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Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses

Cited by 8 publications

References 94 publications

Synthesis of optically pure ant pheromones with high enantiomeric purity.

Synthesis of optically pure ant pheromones with high enantiomeric purity.

meta‐C−H Arylation of Aniline Derivatives via Palladium/ S,O‐Ligand/Norbornene Cooperative Catalysis

meta‐C−H Arylation of Aniline Derivatives via Palladium/ S,O‐Ligand/Norbornene Cooperative Catalysis

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