Lewis Acid Catalyzed Solvent Switching Enabled Diastereodivergent Hydroimination of Bicyclo[1.1.0]butanes
Abstract A Lewis acid catalyzed, solvent-switching diastereodivergent hydroimination of acyl bicyclo[1.1.0]butanes with diphenylmethanimine is reported. Using a rhodium Lewis acid catalyst, the reaction proceeds with excellent and predictable diastereocontrol simply by changing the solvent: in toluene, the corresponding anti 1,3-disubstituted cyclobutanes are formed with >20:1 diastereomeric ratio (d.r.), whereas switching to HFIP reverses the diastereochemical outcome to deliver the syn products. Broad functional group tolerance is demonstrated across a range of aryl- and alkyl-substituted acylbicyclobutanes. Gram-scale reactions, product deprotection to free amines, and a practical sequence for imidazole auxiliary removal further highlight their synthetic utility.
Authors
- Qitao Tan (ORCID: https://orcid.org/0000-0002-6220-651X)
- Shipeng Luo
- Sicong Tu (ORCID: https://orcid.org/0000-0002-6914-6660)
- Jian Li (ORCID: https://orcid.org/0000-0002-3136-5112)
- Yanhong Song (ORCID: https://orcid.org/0000-0002-4019-8213)
- Zijun Zhou (ORCID: https://orcid.org/0000-0001-6542-1429)
- Yunzhi Xie
- Lingfang Wu
- Zhihao Liu (ORCID: https://orcid.org/0009-0009-7702-598X)
- Zetong Liu
Institutions
- Shanghai University (CN)
- Jiangsu University of Science and Technology (CN)
- Gannan Medical University (CN)
- Jiangsu University of Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-09-10
- DOI
- https://doi.org/10.1021/acs.orglett.6c03168
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China