Nickel-Catalyzed Enantioselective Reductive <i>N</i>-Cyclization–Thiolation Reaction of Alkene-Tethered Oxime Esters and Disulfides

Asymmetric aza-Heck cyclization and coupling reactions offer efficient access to enantioenriched <i>N</i>-heterocycles, yet the current studies focus primarily on sequential C-N and C-C bond formation. Herein, we report an enantioselective reductive aza-Heck cyclization followed by a C-S coupling sequence, ultimately yielding sulfide-containing enantioenriched pyrrolines. The reaction is conducted under mild conditions and tolerates broad functionalities including alkynes, phenols, anilines, amides, nitriles, and bromides.

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Publication Details

Journal
Organic Letters
Published
2024-09-27
DOI
https://doi.org/10.1021/acs.orglett.4c03273
Citations
9
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.25

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article

Nickel-Catalyzed Enantioselective Reductive N-Cyclization–Thiolation Reaction of Alkene-Tethered Oxime Esters and Disulfides

Xing‐Zhong Shu, Qi-Wei Yao, Yiyang Huang, Kai Yin et al.
9 citations
Organic Letters
Sulfur-Based Synthesis Techniques
2.25
article

Nickel-Catalyzed Enantioselective Reductive N-Cyclization–Thiolation Reaction of Alkene-Tethered Oxime Esters and Disulfides

Xing‐Zhong Shu, Qi-Wei Yao, Yiyang Huang, Kai Yin, Xiaobo Pang, Jun-Peng Nie
article en
9 citations

Abstract

Asymmetric aza-Heck cyclization and coupling reactions offer efficient access to enantioenriched <i>N</i>-heterocycles, yet the current studies focus primarily on sequential C-N and C-C bond formation. Herein, we report an enantioselective reductive aza-Heck cyclization followed by a C-S coupling sequence, ultimately yielding sulfide-containing enantioenriched pyrrolines. The reaction is conducted under mild conditions and tolerates broad functionalities including alkynes, phenols, anilines, amides, nitriles, and bromides.

Organic LettersVol. 26(40)
Lanzhou University (CN), Southeast University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 12%
Sulfur-Based Synthesis Techniques
2.25
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