Highly stereoselective formation of E-enones via Au-catalyzed reactions of propargylic esters

ORGN 456

Shaozhong Wang, Meng Yu, yum2@unr.nevada.edu, and Liming Zhang, lzhang@unr.edu. Department of Chemistry, University of Nevada, Reno, 1664 North Virginia Street, MS 216, Reno, NV 89557
We report here, as an alternative to the HWE reaction, a highly efficient and versatile method of enone synthesis. From readily available propargylic esters, E-enones were formed exclusively with excellent yields in the presence of Au catalyst. This reaction undergoes Au-catalyzed sequential 3,3-rearrangement of propargylic esters and hydrolysis of the in situ generated allenylic esters.

 

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