Three-component cycloaddition reaction of two enynes with one diene to form eight-membered carbocycles

ORGN 458

Sang Ick Lee, sangick21@hanmail.net, Se Yeoun Park, chem1189@snu.ac.kr, and Young Keun Chung, ykchung@plaza.snu.ac.kr. Department of Chemistry, School of Chemistry and the Center for Molecular Catalysis, College of Natural Sciences, Seoul National University, San 56-1, Shillim-dong, Kwanak-ku, Seoul, 151-747, South Korea
For the synthesis of eight-membered ring compounds, transition metal catalyzed cycloaddition reactions including [4+2+2], [5+2+1], [6+2], and [4+4] cycloadditions have been reported. The known transition metal catalyzed [4+2+2]reactions are bimolecular and three component cycloaddition of enynes with 1,3-butadiene, diynes with alkynes, diynes with 1,3-butadienes, or dienynes to dimers. We have recently developed a new intermolecular Rh complex/AgX catalyzed [4+2+2]cycloaddition of enynes with butadiene that is a tri-moleuclar cycloaddition. In addition, the [4+2+2]cycloaddition product was subjected to ring-closing metathesis yielding the corresponding bicyclic tetraene in one synthetic step.
 

Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006