Diastereoselective three component aza-Diels-Alder reaction catalyzed by heteropolyacids under microwave conditions

ORGN 693

Dmitry Borkin, dmitry.borkin001@umb.edu, Department of Chemistry, University of Massachusetts at Boston, 100 Morrissey Blvd., Boston, MA 02125, Elena Morzhina, Department of Chemistry, University of Massachusetts, Boston, 100 Morissey Blvd, Boston, MA 02125, and Bela Torok, bela.torok@umb.edu, Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA 02125.
Acetylcholinesterase inhibitors represent an important group of small molecule drug candidates against Alzheimer's Disease. Herein, we describe the first efficient microwave-assisted three component diastereoselective synthesis of azabicyclo[2.2.2]octan-5-ones by a silicotungstic acid–catalyzed aza-Diels–Alder cyclization. The one-pot process involves the formation of the in situ generated Schiff base and its immediate cyclization with cyclohex-2-enone. The short reaction time, high yields and excellent diastereoselectivity make this method of annulation both practical and attractive for the synthesis of the target compounds.

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009