ORGN 374 |
New approaches to nitrogen-containing bicyclic scaffolds from iminium ion precursors
| Yu Chen, Department of Chemistry, University of Toronto, 80 St. George Street, Lash Miller Building, Toronto, ON M5S 3H6, Canada and Andrei K. Yudin, Davenport Research Laboratories, Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada. |
Our interests in multistep organic synthesis are in the area of stereoselective construction of small organic molecules containing nitrogen. Functionalized piperidines, pyrrolidines, azetidines, and aziridines are at the center of attention. We recently developed several strategies for the synthetic elaboration of iminium ion precursors produced via anodic electrochemistry. Surprisingly stable a-alkoxylated N-H amides serve as convenient building blocks towards a wide range of nitrogen-containing bicyclic compounds. The mild reaction conditions during N-acyliminium precursor transfer allow us to elaborate the iminium ions at late stages of synthesis. Several approaches that include stereoselective cation/p cyclizations, Diels-Alder reactions, intramolecular amination and tandem sequences, will be discussed. |
| |
|
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
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
|