Memory of chirality in the transannular cyclization of cyclodecenyl radicals

ORGN 299

Jackline E. Dalgard and Scott D. Rychnovsky. Department of Chemistry, University of California, Irvine, 516 Rowland Hall, Irvine, CA 92697-2025
The transannular cyclization of a cyclodecenyl radical generated by photolysis of a mixed pyridine-2-thione oxalate is reported. An enantioenriched radical precursor is employed to generate a secondary cyclodecenyl radical which undergoes a 5-exo cyclization to produce scalemic bicyclo[5.3.0]decanes. This methodology is a route into the hydroazulene skeleton, but more notably demonstrates conformational memory of an unstabilized secondary radical. This transformation exemplifies the increasing utility of radicals in stereoselective C-C bond forming reactions.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Tuesday, September 9, 2003 Sheraton New York -- Royal Ballroom B, Oral

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003