Expanding the Scope of Donor/Acceptor Carbenoids

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With this award, the Chemical Synthesis program is supporting fundamental research of Professor Huw M. L. Davies at Emory University. Professor Davies and his students will employ chiral catalysts for the development of new enantioselective methods in organic synthesis. The study explores reactions induced by vinylogous reactions of metal-stabilized vinylcarbenes and has the potential of generating entirely new transformations in an enantioselective manner. The vinylogous reactions of vinylcarbenes are not yet well understood and these studies are expected to contribute to the fundamental understanding of rhodium carbene chemistry. Professor Davies will integrate the research and educational components of this project within several new initiatives for developing a collaborative and supportive environment for academic researchers. A new Chemistry Research & Diversity Program is planned which will bring professors from minority universities with 2 of their students to work on summer research projects. A robust student-mentoring plan has been designed to ensure the students become experts in their specific area of research and develop the breadth of experience and the communication skills necessary to be highly effective in their future careers. Professor Davies has developed many outreach activities available to his students such as the Spelman Journal Club, science cafes, the Atlanta Science Festival, Chemical Innovator Lecture Series, videoconference short courses, and career development lectures by visiting industrial speakers. In this research, synthetic transformations of metal vinylcarbenes, proceeding by an initial reaction occurring at the vinylogous position of the vinylcarbene, will be explored. Methods will be developed to control the site of reactivity of the metal vinylcarbenes by using either gold catalysts or sterically bulky dirhodium catalysts. A number of novel stereoselective protocols of limited prior precedence will be examined, including [4+3] cycloadditions, [4+2] cycloadditions and crotylations, which will open up new possibilities for the rapid construction of complex target molecules.