Cobalt-Catalyzed Enantioselective Cross-Electrophile Couplings: Stereoselective Syntheses of 5-7-Membered Azacycles

Zhaoming Ma; Wenqiang Xu; Yun-Dong Wu; Jianrong Steve Zhou

doi:10.1021/jacs.3c02829

Cobalt-Catalyzed Enantioselective Cross-Electrophile Couplings: Stereoselective Syntheses of 5-7-Membered Azacycles

J Am Chem Soc. 2023 Aug 2;145(30):16464-16473. doi: 10.1021/jacs.3c02829. Epub 2023 Jul 21.

Authors

Zhaoming Ma¹, Wenqiang Xu², Yun-Dong Wu², Jianrong Steve Zhou¹

Affiliations

¹ State Key Laboratory of Chemical Oncogenomics, Guangdong Provincial Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, 2199 Lishui Road, Nanshan District, Shenzhen 518055, China.
² Laboratory of Computational Chemistry and Drug Design, State Key Laboratory of Chemical Oncogenomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.

PMID: 37477355
DOI: 10.1021/jacs.3c02829

Abstract

Cobalt complexes of chiral pyrox ligands catalyzed enantioselective reductive couplings of nonconjugated iododienes with aryl iodides or alkenyl bromides. The reaction enabled stereoselective syntheses of 5-7-membered azacycles carrying quaternary stereocenters. Mechanistically, cross-electrophile selectivity originated from selective coupling of alkylcobalt(I) complexes generated after cyclization with aryl iodides.