Silacyclobutane oxidations in organic synthesis

ORGN 294

Hubert T. C. Lam, Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL-32306, Tallahassee, FL FL-32306 and Gregory B. Dudley, Department of Chemistry and Biochemistry, Florida State University, Florida State University, Tallahassee, FL 32306.
Due to their strain-release Lewis acidity, silacyclobutanes (siletanes) show enhanced reactivity in reactions such as the Mukaiyama aldol and aldehyde allylation. In efforts to identify novel applications of these substrates in organic synthesis, we discovered that the C-Si bond of a wide range (aryl, alkenyl, alkyl) of these silacycles can be mildly oxidized under the Tamao reaction protocol in high to excellent yields.

Preliminary results and progress in the synthesis of a natural flavanone 2 using this methodology will be discussed. Also, the design of a novel para-siletanylbenzyl (PSB) 3 protecting group will be mentioned.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- 201A, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004