Mild C–C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles
Hai Huang, Tianyu Zhang, Jianwei Sun
Abstract
Abstract Mild oxetane opening by soft carbon nucleophiles has been developed for efficient C−C bond formation. In the presence of LiNTf 2 or TBSNTf 2 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.
Topics & Concepts
OxetaneNucleophileChemistryKeteneIntramolecular forceCatalysisSilylationRing (chemistry)Medicinal chemistryStereochemistryOrganic chemistrySynthetic Organic Chemistry MethodsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods