Solvent- or Base-Controlled Diastereoselectivity and Chemoselectivity for the Reaction of Ketenimine Zwitterionic Salts

Weiguang Yang; Guanrong Li; Zixin Huang; Qiaoli Luo; Hui Luo

doi:10.1002/cjoc.202400723

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (1) : 67 -72. DOI: 10.1002/cjoc.202400723

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Solvent- or Base-Controlled Diastereoselectivity and Chemoselectivity for the Reaction of Ketenimine Zwitterionic Salts

Weiguang Yang ¹^,^†
, Guanrong Li ¹
, Zixin Huang ¹
, Qiaoli Luo ²^,^†
, Hui Luo ¹^,^†

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Abstract

Comprehensive Summary:Ketenimine zwitterionic salt (KZS), a novel and stable ketenimine precursor, is still underexplored in the realm of chemical synthesis. In this study, we demonstrate the transformation of pyrrole derivatives through the cyclization of KZS with α-aminoketones. The diastereoselectivity of this reaction is influenced by the solvent, enabling the isolation of 3-hydroxypyrrolidine diastereomers with the highest reported dr value of 21 : 1. Furthermore, the chemoselectivity is modulated by the choice of base, yielding 2-aminopyrrole derivatives as the major products. This research offers a sustainable approach to harnessing the potential of KZS in organic synthesis, contributing to a greener chemical process.

Keywords

Diastereoselectivity / Chemoselectivity / Ketenimine zwitterionic salts / Solvent-controlled / Base-controlled / α-Aminoketones / 2-Aminopyrrole / 3-Hydroxypyrrolidine / Cyclization

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Weiguang Yang, Guanrong Li, Zixin Huang, Qiaoli Luo, Hui Luo. Solvent- or Base-Controlled Diastereoselectivity and Chemoselectivity for the Reaction of Ketenimine Zwitterionic Salts. Chinese Journal of Chemistry, 2025, 43(1): 67-72 DOI:10.1002/cjoc.202400723