New methodology for the synthesis of 1,2-dioxolanes by annulation of peroxycarbenium ions with olefins

ORGN 616

Armando Ramirez, apramire@uci.edu and Keith A. Woerpel, kwoerpel@uci.edu. Department of Chemistry, University of California, Irvine, Irvine, CA 92717-2025
A new reaction was developed for the efficient synthesis of 1,2-dioxolanes 2. Treatment of silylated peroxyketal 1 with an olefin followed by addition of SnCl4 afforded cyclic peroxides 2 in excellent yields. Peroxyketals 1 were prepared in two steps in good yield from the corresponding ketones. 1,2-Dioxolanes 2 can be further functionalized to obtain carboxylic acids, esters and alcohols whose structures resemble natural products such as the plakinic acids.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005