Synthesis of substituted cyclopentenones via [4 + 1] annulation reactions of (trialkylsilyl)vinylketenes

ORGN 298

Christopher P. Davie and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139
(Trialkylsilyl)vinylketenes react with carbenoid reagents of the general type ":C(R)Z" in a [4 + 1] annulation leading to substituted cyclopentenones. A new variant of this strategy will be reported based on benzotriazole derivatives, and the scope, limitations, mechanism, and stereochemical course of this process will be described.

 

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