Chemoselective Synthesis of α‑Tertiary\nHydroxy Oximes via Photochemical 1,3-Boronate Rearrangement

Tertiary\nalcohols with adjacent nucleophilic labile groups are\nprevalent in bioactive molecules but are challenging to synthesize.\nHerein we introduce a direct, protecting group-free method to access\nα-tertiary hydroxy oximes via photochemical 1,3-boronate rearrangement.\nThis reaction delivers high yields (up to 94%) using readily available\nboronic acids, is scalable to gram quantities, and allows for further\nderivatization to other nitrogen-containing molecules.

Publication Details

Journal
Figshare
Published
2024-09-09
DOI
https://doi.org/10.1021/acs.orglett.4c02353.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

Chemoselective Synthesis of α‑Tertiary\nHydroxy Oximes via Photochemical 1,3-Boronate Rearrangement

Figshare
Mycorrhizal Fungi and Plant Interactions
article

Chemoselective Synthesis of α‑Tertiary\nHydroxy Oximes via Photochemical 1,3-Boronate Rearrangement

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Abstract

Tertiary\nalcohols with adjacent nucleophilic labile groups are\nprevalent in bioactive molecules but are challenging to synthesize.\nHerein we introduce a direct, protecting group-free method to access\nα-tertiary hydroxy oximes via photochemical 1,3-boronate rearrangement.\nThis reaction delivers high yields (up to 94%) using readily available\nboronic acids, is scalable to gram quantities, and allows for further\nderivatization to other nitrogen-containing molecules.

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Openalex Percentile: Top 59%
Mycorrhizal Fungi and Plant Interactions
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Chemoselective Synthesis of α‑Tertiary\nHydroxy Oximes via Photochemical 1,3-Boronate Rearrangement · Figshare (2024) | TGRS Research Map | TGRS