Applications of iminoacetonitrile intramolecular [4 + 2] cycloadditions in organic synthesis

ORGN 287

Kevin M. Maloney, kmaloney@mit.edu and Rick L. Danheiser. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139
Iminoacetonitriles participate as reactive dienophiles in intramolecular [4 + 2] cycloadditions leading to quinolizidines and indolizidines. The resultant α-amino nitrile cycloadducts are versatile synthetic intermediates that can be further elaborated by stereoselective alkylation, reduction, and Bruylants reactions. This talk with focus on the development of reagents that promote cycloadditions under exceptionally mild conditions, the stereochemical course of the reaction, and the synthetic elaboration of the cycloadducts.

 

New Reactions and Methodology
1:00 PM-5:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006