Professor John P. Wolfe of the University of Michigan is supported by the Chemical Synthesis Program in the Division of Chemistry to carry out research on the development of new chemical reactions for the stereocontrolled assembly of tertiary alpha-hydroxy esters. These functional groups are found in many biologically active molecules as well as important building blocks for complex molecule synthesis. The research is focused on the invention of new techniques to generate reactive enediolates and the investigation of new nucleophilic reactions of enediolates for the preparation of molecules that contain 1-2 quaternary stereocenters. In addition, the research is also directed towards the utilization of new carbon-carbon bond-forming reactions between nucleophilic enediolates and carbon-centered electrophiles for the synthesis of complex carbocyclic and heterocyclic molecules. These new reactions will provide access to valuable organic compounds that cannot easily be prepared in a stereocontrolled fashion with existing methods.
The development of new reactions allows chemists to shorten synthetic sequences, saving time, money, and natural resources. This ultimately benefits society by providing important chemicals such as pharmaceuticals at an affordable cost and in an environmentally friendly manner. This research will lead to streamlined routes to compounds with known utility, and will also give access to new compounds that cannot be easily prepared with existing methods. This will afford many opportunities for the discovery of new, useful molecules with applications in fields such as pharmaceuticals, agrochemicals, or materials. The research described above will also provide excellent training to both graduate and undergraduate students, who will master concepts and skills in organic synthesis and synthetic methods development. Upon completion of their training, these students will be well positioned to enter the workforce as productive scientists in industrial, government, or academic laboratories.