A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products

Hai Huang; Wen Yang; Zuliang Chen; Zengwei Lai; Jianwei Sun

doi:10.1039/c9sc03843d

A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products

Chem Sci. 2019 Aug 26;10(41):9586-9590. doi: 10.1039/c9sc03843d. eCollection 2019 Nov 7.

Authors

Hai Huang¹, Wen Yang², Zuliang Chen², Zengwei Lai², Jianwei Sun^{1

2}

Affiliations

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology , School of Petrochemical Engineering , Changzhou University , Changzhou 213164 , China . Email: sunjw@ust.hk.
² Department of Chemistry and Shenzhen Research Institute , The Hong Kong University of Science and Technology , Clear Water Bay , Kowloon , Hong Kong SAR , China.

Abstract

A new catalytic protocol for the expedient synthesis of oxazolines from oxetanes is disclosed. This mild process complements the conventional oxazoline synthesis based on non-catalytic cyclization of β-hydroxy or unsaturated amides. It is also a new addition to the reactivity profile of oxetanes leading to heterocycles. In the presence of In(OTf)₃, various 3-amido oxetanes underwent smooth intramolecular cyclization to form the corresponding 2-oxazolines, including some valuable oxazoline-based bidentate ligands. This protocol also provides rapid access to various natural products and antibacterial molecules.