Lewis Acid Catalyzed Solvent Switching Enabled Diastereodivergent Hydroimination of Bicyclo[1.1.0]butanes
Abstract
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.
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Authors: Lingfang Wu, Zetong Liu, Sicong Tu, Shipeng Luo, Zhihao Liu, Yanhong Song, Yunzhi Xie, Qitao Tan, Jian Li, Zijun Zhou
Institutions: Gannan Medical University, Jiangsu University of Science and Technology, Shanghai University, Jiangsu University of Technology