ol1c02931_si_001.pdf (5.79 MB)
Catalytic Asymmetric [3 + 2] Annulation of Hantzsch Esters with Racemic N‑Sulfonylaziridines
journal contributionposted on 2021-10-05, 15:16 authored by Guo-Sheng Zhu, Pei-Jun Yang, Chen-Xue Ma, Gaosheng Yang, Zhuo Chai
Hantzsch esters (HEs) served as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers including all-carbon quaternary centers in excellent yields and enantiopurities and moderate-to-excellent diastereoselectivities. Mainly dependent upon the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.