Asymmetric syntheses and bio-evaluation of novel chiral esters derived from substituted tetrafluorobenzyl alcohol

Xu, Shicheng; Li, Huangyong; Wang, Xiaohui; Chen, Changshui; Cao, Minhui; Cao, Xiufang

doi:10.1016/j.bmcl.2014.04.055

Cited by 3 publications

(2 citation statements)

References 14 publications

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“…Subsequently, a scale‐up of this direct arylation was targeted in order to illustrate the potential of this methodology for the expedient two‐step synthesis of a biologically active bioisoster of permethrin 5 (Scheme ) . Accordingly, the direct functionalization of 1 i was conducted at 0.5 g scale with no significant alteration of the reaction outcome delivering 3 iK in 91 % yield and high diastereoselectivity of 9:1.…”

Section: Figurementioning

confidence: 61%

“…Recently, due to the extensive use of these insecticides, alarming upsurge of resistance has been witnessed and thus the parent molecular scaffolds with comparable or improved biological activities are urgently requested. Following such a goal, linear analogues of pyrethroids were recently proposed and their promising biological activities were disclosed . However, an asymmetric synthesis of these scaffolds is rather complex, clearly hampering their large screening.…”

Section: Figurementioning

confidence: 99%

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Stereoselective Sulfinyl Aniline‐Promoted Pd‐Catalyzed C−H Arylation and Acetoxylation of Aliphatic Amides

Jerhaoui

Djukic

Wencel‐Delord

et al. 2017

Chemistry A European J

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Stereoselective functionalization of aliphatic C-H bonds presents a great challenge. Following this target, we disclose herein an original strategy towards direct arylation of aliphatic chains at ß-methylene position based on a use of amide-sulfoxide bicoordinating directing group. Although moderate to high chiral induction (up to 9:1 d.r.) is achieved, diastereomerically pure compounds may be afforded by simple separation of diastereomeric products by silica gel chromatography. Accordingly, this reaction allows preparation of a large scope of high-value scaffolds in synthetically useful yields while recyclable character of our chiral auxiliary brings an additional benefit. A potential of this methodology to build up original molecules by sequential diarylation and expedient (two step) synthesis of a biologically active compound are further disclosed. Finally a first example of stereoselective direct acetoxylation of aliphatic chains is reported.

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Section: Figurementioning

confidence: 61%

Section: Figurementioning

confidence: 99%

Stereoselective Sulfinyl Aniline‐Promoted Pd‐Catalyzed C−H Arylation and Acetoxylation of Aliphatic Amides

Jerhaoui

Djukic

Wencel‐Delord

et al. 2017

Chemistry A European J

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Mg-Prompted Polyfluoroarene C–H Functionalization: Formal Synthesis of Transfluthrin, Fenfluthrin, and Tefluthrin

et al. 2015

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Directing group and transition metal free C-H bond functionalization of a simple molecule is an ideal but challenging chemical transformation. Herein, we report a general Mg-prompted approach to synthesize versatile polyfluoroaryl carbinols at ambient temperature via polyfluoroarene C-H bond addition to aldehydes, which featured excellent monoaddition selectivity and broad functional group compatibility. The usefulness of this practical and efficient method was demonstrated in gram-scale formal synthesis of pyrethroid insecticides transfluthrin, tefluthrin, and fenfluthrin.

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Tetrafluorobenzyl Alcohol-Oriented Novel (S)-Enantiomeric Esters: Synthesis and Structure-Activity Relationship

Wang

et al. 2019

CBC

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Background: Using constantly and widely chemistry insecticides has resulted in a selection burden and favored tolerance development in various insect species. Particularly, pyrethroids are the only one which can be used for net impregnation either ITNs or LLIN as yet, however, the excessive use of pyrethroids has led to many cases of insect resistance in worldwide. Therefore, it is urgent to develop novel insecticides fighting against this sort of resistance. Methods: Based on the preliminary studies, we explored a straightforward highly stereoselective method to achieve the novel chiral ester derivatives by using Oppolzer’s 10,2-camphorsultam as chiral controlling reagent. Results: A series of tetrafluorobenzyl alcohol oriented (S)-enantiomeric esters were designed and synthesized by the asymmetric synthesis. All the compounds exhibited moderate yields, and the original synthesized compounds have been evaluated for their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and D-trans-phenothrin, and some compounds presented excellent insecticidal activities. Conclusion: The bioassay illustrated that some of the compounds exhibit obviously insecticidal activities against Plutella xylostella, especially, the insecticidal activity of compound 5i was as good as commercial fenvalerate and D-trans-phenothrin, which can be used as a lead compound for further optimization.

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Asymmetric syntheses and bio-evaluation of novel chiral esters derived from substituted tetrafluorobenzyl alcohol

Cited by 3 publications

References 14 publications

Stereoselective Sulfinyl Aniline‐Promoted Pd‐Catalyzed C−H Arylation and Acetoxylation of Aliphatic Amides

Stereoselective Sulfinyl Aniline‐Promoted Pd‐Catalyzed C−H Arylation and Acetoxylation of Aliphatic Amides

Mg-Prompted Polyfluoroarene C–H Functionalization: Formal Synthesis of Transfluthrin, Fenfluthrin, and Tefluthrin

Tetrafluorobenzyl Alcohol-Oriented Novel (S)-Enantiomeric Esters: Synthesis and Structure-Activity Relationship

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