Synthetic applications of an ethynyl aziridine ring opening reaction

ORGN 543

Erin M. Forbeck, eforbeck@sas.upenn.edu and Madeleine M. Joullié, mjoullie@sas.upenn.edu. Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA 19104-6323
Chiral tertiary alkyl-aryl ethers are important targets and intermediates in organic synthesis. An ethynyl aziridine ring opening reaction to form this functionality has been discovered. This reaction has been applied to the total synthesis of ustiloxin D, allowing for a more convergent synthetic route due to its functional group tolerance. This strategy has been further investigated using a variety of functionalized aziridines and phenols to determine the scope of the reaction to form these hindered ethers. Other nucleophiles have been employed to encompass a broader range of functionalities. Synthetic applications of this reaction will also be presented.

 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008