The innovation engine for new materials

Carl Peterson

Carl Peterson

Major: 

Chemistry

University: 

Fort Lewis College

Mentor(s): 

Donal Wenz

Faculty Sponsor(s): 

Professor Javier Read de Alaniz

Faculty Sponsor's Department(s): 

Chemistry and Biochemistry

Project Title: 

DEVELOPMENT OF AN AZA-PIANCATELLI REARRANGEMENT

Project Description: 

The cyclopentenone framework is found in a large number of natural products including aflatoxins and several prostaglandins and thus provides great opportunity for further development of currently used methodologies.  An Aza-Piancatelli rearrangement of furylcyclopropanes was developed.  The reactions were performed open to air with commercially available Dy(OTf)3.  Various aniline substrates were investigated to determine the scope of this rearrangement.  Cyclopropanes were found to be a good alternative in this rearrangement to promote ring opening rather than the creation of a charge and subsequently the loss of water.  I was successful in the development of a cyclopropane activated rearrangement.