Org. Lett., 7 (21), 4617 -4620, 2005. 10.1021/ol051703u S1523-7060(05)01703-7
Web Release Date: September 23, 2005

Copyright © 2005 American Chemical Society

Synthesis of 1,2-Dioxolanes by Annulation Reactions of Peroxycarbenium Ions with Alkenes

Armando Ramirez and K. A. Woerpel*

Department of Chemistry, University of California, Irvine, California 92697-2025

kwoerpel@uci.edu

Received July 19, 2005

Abstract:

The annulation reactions of alkenes with peroxycarbenium ions enable the synthesis of a variety of functionalizable 1,2-dioxolanes. Triethysilyl-protected peroxycarbenium ions proved to be optimal for the annulation reaction. Using this method, plakinic acid analogues can be synthesized in three steps from the corresponding ketone and alkene.


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