Rh(II)-catalyzed olefin aziridination: Toward the synthesis of N-methylwelwitindolinone C

ORGN 2

Kiran Guthikonda, kg37@stanford.edu, Brian J. Caliando, and Justin Du Bois, jdubois@stanford.edu. Department of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305
An efficient method for stereospecific intra- and intermolecular Rh(II)-catalyzed aziridination will be presented. This chemistry enables the installation of nitrogen in a wide variety of olefinic substrates to give N-alkoxysulfonyl aziridines. Ring-opening reactions of the aziridine products display their usefulness for producing 1,2-difunctionalized amine derivatives. Application of this method is currently aimed at the synthesis of welwitindolinone C, one member of a unique family of marine oxindole alkaloids isolated from the cyanobacteria Hapalosiphon welwitschii.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 134, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006