Chemoselective Synthesis of α-Tertiary Hydroxy Oximes via Photochemical 1,3-Boronate Rearrangement
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.
Authors
- Yiyun Chen (ORCID: https://orcid.org/0000-0003-0916-0994)
- Yixin Zhang (ORCID: https://orcid.org/0000-0002-0927-6981)
- Peng Zou (ORCID: https://orcid.org/0000-0002-8474-0553)
- Ruijing Cai
Institutions
- ShanghaiTech University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-09
- DOI
- https://doi.org/10.1021/acs.orglett.4c02353
- Citations
- 3
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Youth Innovation Promotion Association of the Chinese Academy of Sciences
- Program of Shanghai Academic Research Leader