Former BRG Member:

Matthew S. Burge (Post-Doctoral Research Associate) [2005-2007]

Matt Burge obtained a B.A. from Monmouth College (Monmouth, Illinois) in 2000, under the instruction of Dr. Peter Gabauer. Using atomic absorption techniques, Matt determined the concentration of metal ions in local streams polluted from waste run-off. In 2005, Matt obtained a Ph.D. in Chemistry from the University of Illinois at Chicago working under the guidance of Prof. Duncan J. Wardrop. During his graduate career, Matt studied the generation of azaspirodienones through diastereoselective cyclization of N-acyl-N-methoxy nitrenium ions, generated from the corresponding amides and PIFA (a hyper- valent iodine reagent). Furthermore, Matt investigated the diastereoselective cyclization of nitrenium ions to achieve the total synthesis of (–)-dysibetaine, a marine neurotoxin. During his work on (–)-dysibeatine, Matt also explored the ozonolytic cleavage of 2,5-spirodienones as a means to secure beta-hydroxyesters which can be further manipulated to provide useful 2-hydroxymethyl amino acids. Matt worked in the Blakemore Research Group from September 2005 to January 2007 and investigated the in situ generation of enantioenriched chiral carbenoids by sulfoxide ligand exchange and the deployment of such species for stereospecific reagent controlled homologation (StReCH) of boronic esters.

Blakemore,* P. R.; Burge, M. S; Sephton, M. A. "Competing Reaction Pathways from alpha-Halo-alpha-protioalkyl Aryl Sulfoxides Initiated by Organometallic Reagents," Tetrahedron Lett. 2007, 48, 3999-4002. [LINK]

Blakemore,* P. R.; Burge, M. S. "Iterative Stereospecific Reagent Controlled Homologation of Pinacol Boronates by Enantioenriched alpha-Chloroalkyllithium Reagents," J. Am. Chem. Soc. 2007, 129, 3068-3069. [LINK]

Wardrop,* D. J.; Burge, M. S."Nitrenium Ion Azaspirocyclization-Cyclohexadienone Cleavage: A New Synthetic Strategy for the Stereocontrolled Preparation of Highly Substituted Lactams and N-Hydroxy Lactams," J. Org. Chem. 2005, 70, 10271-10284. [LINK]

Wardrop,* D. J.; Burge, M. S."Total Synthesis of (–)-Dysibetaine via a Nitrenium Ion Cyclization-Dienone Cleavage Strategy," Chem. Commun. 2004, 1230-1231. [LINK]

Wardrop,* D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A."pi-Face Selective Azaspirocyclization of omega-(Methoxyphenyl)-N-methoxyalkyl Amides," Tetrahedron Lett. 2003, 44, 2587-2591. [LINK]

 

Last modified: October 10, 2008 (PRB)