Bronsted acid-catalyzed amidation of imines

ORGN 404

Jon C. Antilla, jantilla@olemiss.edu1, Haile Zhang2, Yong Wang1, Emily B. Rowland1, and Gerald B. Rowland1. (1) Department of Chemistry and Biochemistry, University of Mississippi, Coulter Hall, Room 405, University, MS 38677, (2) Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037
The efficient Brønsted acid-catalyzed addition of amides to imines is reported. General imine amidation conditions using as little as 0.25 mol % of simple Brønsted acids have been developed. A wide range of amides and sulfonamides were utilized in the reaction to provide high yields of the aminal products (up to 98%). Reaction scope as well as possible asymmetric variants will be addressed.

 

Process R&D, Practical Synthesis, and Methodology
1:00 PM-4:20 PM, Tuesday, 15 March 2005 Convention Center -- Room 11A, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005