Enantioselective Intramolecular Oxidative Aminoacetoxylation from Aryl-Substituted Alkene via Chiral Triazole-oxazoline Palladium Complexes

Here, we describe an enantioselective intramolecular oxidative aminoacetoxylation reaction using a palladium catalyst and an aryl-substituted internal alkene compound as the substrate under mild conditions in several hours. The triazole-oxazoline ligand was selected for the asymmetric catalyst. A range of enantioenriched pyrrolidine-derived vicinal amino acetate compounds were synthesized, showing yields from 47% to 84%, diastereomer ratios from 57:43 to 95:5, and enantiomer excesses from 67% to 92%.

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Publication Details

Journal
Organic Letters
Published
2024-10-31
DOI
https://doi.org/10.1021/acs.orglett.4c03248
Citations
4
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.00

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article

Enantioselective Intramolecular Oxidative Aminoacetoxylation from Aryl-Substituted Alkene via Chiral Triazole-oxazoline Palladium Complexes

Jongseok Kang, Zhiguang Song, Dongyuan Ju
4 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.00
article

Enantioselective Intramolecular Oxidative Aminoacetoxylation from Aryl-Substituted Alkene via Chiral Triazole-oxazoline Palladium Complexes

Jongseok Kang, Zhiguang Song, Dongyuan Ju
article en
4 citations

Abstract

Here, we describe an enantioselective intramolecular oxidative aminoacetoxylation reaction using a palladium catalyst and an aryl-substituted internal alkene compound as the substrate under mild conditions in several hours. The triazole-oxazoline ligand was selected for the asymmetric catalyst. A range of enantioenriched pyrrolidine-derived vicinal amino acetate compounds were synthesized, showing yields from 47% to 84%, diastereomer ratios from 57:43 to 95:5, and enantiomer excesses from 67% to 92%.

Organic LettersVol. 26(45)
Jilin University (CN)
Jilin Province Development and Reform Commission
Openalex Percentile: Top 26%
Catalytic C–H Functionalization Methods
1.00
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Enantioselective Intramolecular Oxidative Aminoacetoxylation from Aryl-Substituted Alkene via Chiral Triazole-oxazoline Palladium Complexes — Jongseok Kang, Zhiguang Song, et al. · Organic Letters (2024) | TGRS Research Map | TGRS