Nickel-Catalyzed Enantioselective\nC(sp<sup>3</sup>)–C(sp<sup>3</sup>) Cross-Electrophile Coupling\nof <i>N</i>‑Sulfonyl Styrenyl Aziridines with Alkyl\nBromides

Herein, we report the first example of a highly enantioselective\nalkylative aziridine ring opening. Under the catalysis of a chiral\nnickel/pyridine-imidazoline complex, asymmetric C(sp<sup>3</sup>)–C(sp<sup>3</sup>) cross-electrophile coupling between racemic <i>N</i>-sulfonyl styrenyl aziridines and readily available primary alkyl\nbromides furnishes a variety of highly enantioenriched phenethylamine\nderivatives with complete regiocontrol and good functional group tolerance.\nPreliminary mechanistic studies support a reaction pathway consisting\nof regioselective iodolysis of aziridines <i>in situ</i> and subsequent enantioconvergent coupling of the generated β-amino\nbenzyl iodides with alkyl bromides.

Publication Details

Journal
Figshare
Published
2024-09-04
DOI
https://doi.org/10.1021/jacs.4c08435.s001
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Nickel-Catalyzed Enantioselective\nC(sp3)–C(sp3) Cross-Electrophile Coupling\nof N‑Sulfonyl Styrenyl Aziridines with Alkyl\nBromides

Figshare
Synthesis and Catalytic Reactions
article

Nickel-Catalyzed Enantioselective\nC(sp3)–C(sp3) Cross-Electrophile Coupling\nof N‑Sulfonyl Styrenyl Aziridines with Alkyl\nBromides

article en

Abstract

Herein, we report the first example of a highly enantioselective\nalkylative aziridine ring opening. Under the catalysis of a chiral\nnickel/pyridine-imidazoline complex, asymmetric C(sp<sup>3</sup>)–C(sp<sup>3</sup>) cross-electrophile coupling between racemic <i>N</i>-sulfonyl styrenyl aziridines and readily available primary alkyl\nbromides furnishes a variety of highly enantioenriched phenethylamine\nderivatives with complete regiocontrol and good functional group tolerance.\nPreliminary mechanistic studies support a reaction pathway consisting\nof regioselective iodolysis of aziridines <i>in situ</i> and subsequent enantioconvergent coupling of the generated β-amino\nbenzyl iodides with alkyl bromides.

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Synthesis and Catalytic Reactions
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