Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents

Given the pivotal role of β-(het)arylethylamine moiety in bioactive molecules, the direct amino(het)arylation of alkenes occupies a privileged position in the construction of (het)arylethylamine derivatives. Herein we devise chiral sulfoximines as novel bifunctional reagents which exhibit remarkable efficiency in the challenging asymmetric alkene aminohetarylation reaction, particularly in terms of reactivity and stereo-control. The chiral reagents can be conveniently accessed in gram scale, and efficiently generate N-centered radicals under mild photochemical conditions. The transformation proceeds through enantioselective 1,4-hetaryl migration, ensuring precise chirality transfer from sulfur- to carbon-centers, rendering wide applicability to both aromatic and aliphatic alkenes. Furthermore, the method is straightforward to operate and does not require transition metals or photosensitizers, making it an attractive and practical option.

Authors

Institutions

Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-08-15
DOI
https://doi.org/10.1002/anie.202408177
Citations
24
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
6.00

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents

Yasu Chen, Chen Hui Zhu, Zhu Cao, Sun Yu-qian
24 citations
Angewandte Chemie International Edition
Catalytic C–H Functionalization Methods
6.00
article

Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents

Yasu Chen, Chen Hui Zhu, Zhu Cao, Sun Yu-qian
article en
24 citations

Abstract

Given the pivotal role of β-(het)arylethylamine moiety in bioactive molecules, the direct amino(het)arylation of alkenes occupies a privileged position in the construction of (het)arylethylamine derivatives. Herein we devise chiral sulfoximines as novel bifunctional reagents which exhibit remarkable efficiency in the challenging asymmetric alkene aminohetarylation reaction, particularly in terms of reactivity and stereo-control. The chiral reagents can be conveniently accessed in gram scale, and efficiently generate N-centered radicals under mild photochemical conditions. The transformation proceeds through enantioselective 1,4-hetaryl migration, ensuring precise chirality transfer from sulfur- to carbon-centers, rendering wide applicability to both aromatic and aliphatic alkenes. Furthermore, the method is straightforward to operate and does not require transition metals or photosensitizers, making it an attractive and practical option.

Angewandte Chemie International EditionVol. 63(47)
Shanghai Jiao Tong University (CN), Shanghai Innovative Research Center of Traditional Chinese Medicine (CN), Soochow University (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 3%
Catalytic C–H Functionalization Methods
6.00
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.

Photoinduced Asymmetric Alkene Aminohetarylation with Chiral Sulfoximine Reagents — Yasu Chen, Chen Hui Zhu, et al. · Angewandte Chemie International Edition (2024) | TGRS Research Map | TGRS