Straightforward Synthesis of Spirocyclic Tetrahydrofurans by a Reductive MCR/Iodoetherification Sequence

J Org Chem. 2022 Apr 1;87(7):4971-4980. doi: 10.1021/acs.joc.1c03034. Epub 2022 Mar 21.

Abstract

A straightforward and modular sequence for the synthesis of substituted spirocyclic tetrahydrofurans is described. The strategy relies on a reductive cobalt-catalyzed three-component reaction between a cyclic ketone, an acrylate, and a vinylic bromide followed by an intramolecular iodoetherification of the resulting γ-hydroxyalkene. Some functional group interconversions allowed the preparation of more varied spirocyclic compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Furans*
  • Ketones*
  • Stereoisomerism

Substances

  • Furans
  • Ketones