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

Asymmetric aza-Heck cyclization and coupling reactions offer efficient access to enantioenriched N-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,...

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Veröffentlicht in:Organic letters 2024-09, Vol.26 (40), p.8599-8604
Hauptverfasser: Yao, Qi-Wei, Yin, Kai, Huang, Yi-Yang, Nie, Jun-Peng, Pang, Xiaobo, Shu, Xing-Zhong
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Sprache:eng
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Zusammenfassung:Asymmetric aza-Heck cyclization and coupling reactions offer efficient access to enantioenriched N-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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03273