Intramolecular [4+2] cycloaddition of conjugated enynes with ynamides: An efficient strategy for the synthesis of substituted indolines and indoles

ORGN 378

Joshua R. Dunetz and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139

The intramolecular [4+2] cycloaddition of conjugated enynes with ynamides provides an efficient synthetic route to indolines and indoles bearing multiple substituents on the six-membered ring. The scope and limitations of this strategy will be discussed, as well as several alternative methods for the efficient assembly of the requisite ynamide cycloaddition substrates.

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions 8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster Sci-Mix 8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003