Chemoselective Synthesis of α-Tertiary Hydroxy Oximes via Photochemical 1,3-Boronate Rearrangement,Organic Letters

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Chemoselective Synthesis of α-Tertiary Hydroxy Oximes via Photochemical 1,3-Boronate Rearrangement
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-09 , DOI: 10.1021/acs.orglett.4c02353
Ruijing Cai _{1,

2} , Peng Zou ₁ , Yixin Zhang ₁ , Yiyun Chen _{1,

2,

3}

Affiliation

Tertiary alcohols with adjacent nucleophilic labile groups are prevalent in bioactive molecules but are challenging to synthesize. Herein we introduce a direct, protecting group-free method to access α-tertiary hydroxy oximes via photochemical 1,3-boronate rearrangement. This reaction delivers high yields (up to 94%) using readily available boronic acids, is scalable to gram quantities, and allows for further derivatization to other nitrogen-containing molecules.

中文翻译：

通过光化学 1,3-硼酸酯重排化学选择性合成 α-叔羟基肟

具有相邻亲核不稳定基团的叔醇在生物活性分子中普遍存在，但合成具有挑战性。在此，我们介绍了一种直接、无保护基团的方法，通过光化学 1,3-硼酸酯重排获得 α-叔羟基肟。该反应使用现成的硼酸实现高产率（高达 94%），可扩展到克级，并允许进一步衍生化为其他含氮分子。

更新日期：2024-09-09

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