Stereoselective Synthesis of Tetrahydropyran-4-ones from Dioxinones Catalyzed by Scandium(III) Triflate

William J. Morris, Daniel W. Custar, and Karl A. Scheidt*
Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208
Org. Lett., 2005, 7 (6), pp 1113–1116
DOI: 10.1021/ol050093v
Publication Date (Web): February 11, 2005
Copyright © 2005 American Chemical Society

Abstract

Abstract Image

A scandium triflate catalyzed, diastereoselective cyclization between aldehydes and β-hydroxy dioxinones has been discovered. This process capitalizes on the untapped nucleophilicity of the embedded enol ether within the dioxinone core. The bicyclic compounds from the resulting cyclization can be isolated, or alternatively, alkoxide nucleophiles can be directly added. This in situ addition fragments the dioxinone rings and delivers the 3-carboxy-substituted tetrahydropyran-4-ones in good yields with high levels of diastereoselectivity.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

SciFinder subscribers: Click to sign in | Not a SciFinder subscriber? Learn more at www.cas.org

Explore by:

History

  • Published In Issue March 17, 2005
  • Received January 17, 2005

Recommend & Share

Related Content

Other ACS content by these authors: