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
- Field-Weighted Citation Impact
- 0.00