N-Tosyloxycarbamates as precursor for enantioselective and catalytic aziridination reactions

ORGN 528

Michael Parmentier, lebelhe@chimie.umontreal.ca and Hélène Lebel, lebelhe@chimie.umontreal.ca. Département de Chimie, Université de Montréal, PO Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada

 

The presence of nitrogen in many natural products illustrates the need for efficient methodologies to form nitrogen derivatives, particularly, chiral aziridines. Our group is interested in the development of novel transition metal-catalyzed reactions. Recently, we have reported that pyridine copper (II) complexes catalyzed the intermolecular aziridination of styrenes with trichloroethyl N-tosyloxycarbamate. The use of such reagents as nitrene precursor has a number of advantages over the hypervalent iodine reagents typically used in aziridination reaction. For instance, no high boiling point organic derivative, such as iodobenzene is produced as a by product, thus simplifying the purification procedure. Furthermore, this method led to troc-aziridines which can be easily deprotected.  A one-pot procedure, in which the troc will be cleaved in-situ, will be described for the formation of free aziridines. Preliminaries studies for the development of an enantioselective version, using chiral ligands, will be also discussed.

 

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007