通过光化学1,3-硼酸酯重排实现α-叔羟基肟的化学选择性合成。
Chemoselective Synthesis of α-Tertiary Hydroxy Oximes via Photochemical 1,3-Boronate Rearrangement.
作者信息
Cai Ruijing, Zou Peng, Zhang Yixin, Chen Yiyun
机构信息
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai 201210, China.
出版信息
Org Lett. 2024 Sep 20;26(37):7795-7799. doi: 10.1021/acs.orglett.4c02353. Epub 2024 Sep 9.
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.
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，我们介绍一种直接的、无需保护基团的方法，通过光化学1,3-硼酸酯重排来制备α-叔羟基肟。该反应使用易于获得的硼酸，产率高（高达94%），可扩大至克级规模，并允许进一步衍生为其他含氮分子。
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