Expanding the scope of Prins cyclization methodology through mechanistic studies

ORGN 672

Ramesh Jasti, Department of Chemistry, University of California at Irvine, 516 Rowland Hall, Irvine, CA 92697-2025 and Scott D. Rychnovsky, srychnov@uci.edu, Department of Chemistry, University of California, Irvine, 516 Rowland Hall, Irvine, CA 92697-2025.
The Prins cyclization is a powerful method to construct functionalized tetrahydropyrans with high levels of stereocontrol. An intervening 2-oxonia Cope rearrangement has been identified and further utilized as a mechanistic probe. Through these mechanistic studies previously unknown elements of stereocontrol for this reaction have been discovered. In addition, support for a tetrahydropyranyl cation is provided.

 

New Reactions and Methodology
1:00 PM-5:00 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