Mild C-C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles

Hai Huang; Tianyu Zhang; Jianwei Sun

doi:10.1002/anie.202013062

Mild C-C Bond Formation via Lewis Acid Catalyzed Oxetane Ring Opening with Soft Carbon Nucleophiles

Angew Chem Int Ed Engl. 2021 Feb 1;60(5):2668-2673. doi: 10.1002/anie.202013062. Epub 2020 Dec 1.

Authors

Hai Huang¹, Tianyu Zhang¹, Jianwei Sun^{1

2}

Affiliations

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, China.
² Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.

PMID: 33459485
DOI: 10.1002/anie.202013062

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.

Keywords: C−C bond formation; Lewis acids; oxetane; ring opening; strained molecules.

Abstract

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