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Mild C–C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles
Author(s) -
Huang Hai,
Zhang Tianyu,
Sun Jianwei
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202013062
Subject(s) - oxetane , nucleophile , chemistry , ketene , intramolecular force , catalysis , silylation , ring (chemistry) , medicinal chemistry , stereochemistry , organic chemistry
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.