Fluorocyclization of Allyl Alcohols and Amines to Access 3-Functionalized Oxetanes and Azetidines

Org Lett. 2021 May 7;23(9):3674-3679. doi: 10.1021/acs.orglett.1c01062. Epub 2021 Apr 21.

Abstract

An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N3 or -OR) plays a crucial role in polarizing the C═C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.

Publication types

  • Research Support, Non-U.S. Gov't