K-10 catalyzed highly diastereoselective aziridination of imines

ORGN 722

Alena Carlson, alena.dc@gmail.com, Chemistry Department, University of Massachusetts at Boston, 100 Morrissey Blvd., Boston, MA 02125, Dmitry Borkin, dmitry.borkin001@umb.edu, Department of Chemistry, University of Massachusetts at Boston, 100 Morrissey Blvd., Boston, MA 02125, and Bela Torok, bela.torok@umb.edu, Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA 02125.
Aziridines are versatile organic molecules due to their ability to undergo highly regio- and stereoselective ring-opening reactions that makes them very useful building blocks in organic synthesis. Aziridine moiety is also found in a variety of biologically active natural products and, furthermore, synthetic aziridines also exhibit useful biological properties. In this work we describe a new heterogeneous catalytic method for the stereoselective preparation of cis-aziridines from imines and ethyl diazoacetate using montmorillonite K-10 as catalyst. The reactions proceed readily at room temperature in short reaction times, providing the products in excellent yields (90%) and exclusive selectivity for the cis diastereomer.

 

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

Sci-Mix
8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

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