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Download fileCatalytic Asymmetric [3 + 2] Annulation of Hantzsch Esters with Racemic N‑Sulfonylaziridines
journal contribution
posted on 2021-10-05, 15:16 authored by Guo-Sheng Zhu, Pei-Jun Yang, Chen-Xue Ma, Gaosheng Yang, Zhuo ChaiHantzsch
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.