Combination of catalytic hydroamination and the Strecker reaction: Applications and mechanistic insight

ORGN 484

Alison V. Lee, alee@chem.ubc.ca and Laurel L. Schafer. Department of Chemistry, University of British Columbia, Rm W300 - 6174 University Blvd., Vancouver, BC V6T 1Z3, Canada
Mechanistic investigations of tandem reactions provide vital insight into the development of new synthetic strategies. The combination of catalytic hydroamination and the Strecker reaction has led to efficient methodologies for the syntheses of many products that are laborious to access through traditional reaction sequences. Hydroamination of terminal alkynes with primary amines yields aldimines with no by-products, such as water. Therefore, these aldimines can be used without isolation in further reactions, including those that may be sensitive to water. This methodology has been used to synthesize a number of novel nitrogen-containing compounds. The mechanism of these tandem reactions has also been probed, and this insight has been applied toward the design of enantioselective versions of these methods.

 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Sci-Mix

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007