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May 11, 2026Organic Letters2 citations

Nucleophiles as Reaction Switches: Dearomative Multifunctionalization of Isoquinoliniums to Rigid Bridged-Ring Architectures

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ZGZerong GUOYQYunlong QinQWQingling Wu

Key Points

  • This research explores how nucleophiles can act as reaction switches in the transformation of isoquinolines.
  • Utilized nucleophiles to achieve dual roles as reaction switches and bridging linkers.
  • Investigated regio-, chemo-, and stereocontrol in the synthesis of complex architectures.
  • Conducted PMI analysis and physicochemical evaluations to assess drug-like properties.
  • Demonstrated the ability to construct rigid bridged-ring architectures from isoquinolines.
  • Achieved precise control over stereochemistry, regioselectivity, and chemoselectivity.
  • Confirmed significant three-dimensionality and favorable drug-like profiles for the new compounds.

Abstract

-rich bridged bis-tetrahydroisoquinolines. Nucleophiles serve dual roles as reaction switches and stereodefined bridging linkers, enabling precise regio-, chemo-, and stereocontrol. This streamlined approach unlocks the full reactive potential of isoquinolines for constructing architecturally complex polycyclic frameworks with broad applicability to carbon-, nitrogen-, and sulfur-centered nucleophiles. PMI analysis and physicochemical evaluation confirm their pronounced three-dimensionality and drug-like profiles.

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Cite This Study

GUO et al. (2026) studied this question.

synapsesocial.com/papers/6a0171473a9f334c28271a7chttps://doi.org/10.1021/acs.orglett.6c01478
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