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

Asymmetric\naza-Heck cyclization and coupling reactions offer efficient\naccess to enantioenriched <i>N</i>-heterocycles, yet the\ncurrent studies focus primarily on sequential C–N and C–C\nbond formation. Herein, we report an enantioselective reductive aza-Heck\ncyclization followed by a C–S coupling sequence, ultimately\nyielding sulfide-containing enantioenriched pyrrolines. The reaction\nis conducted under mild conditions and tolerates broad functionalities\nincluding alkynes, phenols, anilines, amides, nitriles, and bromides.

Publication Details

Journal
Figshare
Published
2024-09-27
DOI
https://doi.org/10.1021/acs.orglett.4c03273.s001
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
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article

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

Figshare
Sulfur-Based Synthesis Techniques
article

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

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Abstract

Asymmetric\naza-Heck cyclization and coupling reactions offer efficient\naccess to enantioenriched <i>N</i>-heterocycles, yet the\ncurrent studies focus primarily on sequential C–N and C–C\nbond formation. Herein, we report an enantioselective reductive aza-Heck\ncyclization followed by a C–S coupling sequence, ultimately\nyielding sulfide-containing enantioenriched pyrrolines. The reaction\nis conducted under mild conditions and tolerates broad functionalities\nincluding alkynes, phenols, anilines, amides, nitriles, and bromides.

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Sulfur-Based Synthesis Techniques
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Nickel-Catalyzed Enantioselective Reductive <i>N</i>‑Cyclization–Thiolation Reaction of Alkene-Tethered\nOxime Esters and Disulfides · Figshare (2024) | TGRS Research Map | TGRS