Mild C-C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles
Hai Huang1, Tianyu Zhang1, Jianwei Sun1,2
1Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, China.
Abstract:
Mild oxetane opening by soft carbon nucleophiles has been developed for efficient C-C bond formation. In the presence of LiNTf2 or TBSNTf2 as catalyst, silyl ketene acetals were found to be effective nucleophiles to generate a wide range of highly oxygenated molecules, which are key substructure in natural products like polyketides. Furthermore, intramolecular oxetane opening by a styrene-based carbon nucleophile via a Prins-type process was also achieved with Sc(OTf)3 as catalyst, leading to efficient formation of the useful 2,3-dihydrobenzo[b]oxepine skeleton.
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