Gold(I)-catalyzed cyclization of enynes bearing an olefinic cycle

ORGN 449

Sang Ick Lee, sangick21@hanmail.net, Soo Min Kim, smlily82@snu.ac.kr, Sun Young Kim, kim99718@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
Tricyclic compounds were synthesized by Rh-NHC and AuCl(PPh3) catalyst with AgSbF6 as co-catalyst. Rh-NHC catalyzed intermolecular [4+2] cycloaddition with 1,6-diyne and 2,3-dimethylbutadiene offered enynes bearing an cyclic olefin very efficiently. AuCl(PPh3) catalyzed enyne isomerization give constrained tricyclic compound at mild condition. Tandem(or sequential) cycloaddition of [4+2] cycloaddition and enyne isomerization gave the desired product at slower activity.
 

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