News & Events

When

Date - April 17, 2019
1:00 pm - 2:00 pm

What

MS Defense
Advisor: Dr. Kimberly Petersen
Talk Title: Asymmetric Synthesis of Novel Spirocycles via a Chiral Phosphoric Acid Catalyzed Desymmetrization

Abstract:

Organic molecules can exist as two mirror images which have the same physical properties but different spatial orientations. Their unique 3-dimensional shape is attributed to an asymmetric or chiral center and can affect the way they react with enzymes or other molecules that exhibit chirality. Considering how challenging it is to synthesize only one of the mirror images, our group focuses on developing methodologies that will make this process easier. In this project we report the asymmetric synthesis of novel molecules that contain a quaternary C spiro center. The methodology used to synthesize these novel spirocycles has been previously developed in our lab and is known as desymmetrization. A chiral Brønsted acid catalyzed desymmetrization method was used to obtain the enantioenriched intermediates which then underwent a second cyclization with an achiral acid.