Halogen-Bond-Assisted NHC-Catalyzed (Dynamic) Kinetic\nResolution for the Atroposelective Synthesis of Heterobiaryls

We report a novel halogen-bond-assisted\nNHC-catalyzed (dynamic)\nkinetic resolution strategy for the synthesis of axially chiral heterobiaryls.\nA class of axially chiral quinolines are prepared efficiently in excellent\nenantioselectivities (≤98% ee) employing 3–5 mol % NHC\ncatalyst. Mechanistic studies reveal the indispensability of 5-bromo-2-iodobenzaldehyde\nin this reaction, in which a pivotal halogen bonding interaction plays\na crucial role in the process.

Publication Details

Journal
Figshare
Published
2024-10-15
DOI
https://doi.org/10.1021/acs.orglett.4c03346.s001
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
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article

Halogen-Bond-Assisted NHC-Catalyzed (Dynamic) Kinetic\nResolution for the Atroposelective Synthesis of Heterobiaryls

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Axial and Atropisomeric Chirality Synthesis
article

Halogen-Bond-Assisted NHC-Catalyzed (Dynamic) Kinetic\nResolution for the Atroposelective Synthesis of Heterobiaryls

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Abstract

We report a novel halogen-bond-assisted\nNHC-catalyzed (dynamic)\nkinetic resolution strategy for the synthesis of axially chiral heterobiaryls.\nA class of axially chiral quinolines are prepared efficiently in excellent\nenantioselectivities (≤98% ee) employing 3–5 mol % NHC\ncatalyst. Mechanistic studies reveal the indispensability of 5-bromo-2-iodobenzaldehyde\nin this reaction, in which a pivotal halogen bonding interaction plays\na crucial role in the process.

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Axial and Atropisomeric Chirality Synthesis
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Halogen-Bond-Assisted NHC-Catalyzed (Dynamic) Kinetic\nResolution for the Atroposelective Synthesis of Heterobiaryls · Figshare (2024) | TGRS Research Map | TGRS