With funding from the Synthesis Program of the Chemistry Division, Professor Jeremy May of the University of Houston is designing and synthesizing catalysts, especially carbon-based catalysts (i.e., "organocatalysts"), that increase the efficiency of carbon-carbon bonds forming reactions with the necessary control of three-dimentional structure. This research is transformative in that the use of such organocatalysts avoids many problems associated with metal-containing catalysts, including toxicity and the expense of precious metals. In addition, this research is providing fundamental insights into the mechanisms of organocatalyzed reactions. Some of these reactions are biologically relevant. Dr. May's new reactions replicate and improve upon natural products that have antibacterial, anticancer, neurological, or immune system-stimulating activity. In addition, the Professor May is partnering with KIPP Sharpstown Junior High to introduce students to experimental chemistry and other physical sciences. The May lab works with disadvantaged and at-risk students to bolster their scientific understanding and desire to prepare for college.
Professor May is designing and synthesizing asymmetric organocatalysts that can promote the conjugate addition of vinyl and aryl boronates to alpha, beta-unsaturated ketones for the synthesis of carbon-carbon (C-C) bonds efficiently and with high levels of stereocontrol. This project is advancing fundamental knowledge of organocatalysis, the reactivity of boronate reagents, and stereoelectronic effects in C-C bond formation. The reagents and intermediates involved are highly tolerant of sensitive chemical functional groups, allowing great diversity in the substrate scope and access to atomic arrangements commonly found in bioactive molecules. The synthesis of sterically encumbered C-C bonds that are otherwise difficult to form is an aim of this project. This research is transformative as the use of organocatalysts and boronates avoids many of the problems associated with transition metal catalysts including a lack of tolerance of heterocycles or heteroatoms. The synthesis of targets and analogs of the indolyl propylene glycol class of natural products, which have been shown to exhibit antibacterial, antimetastatic, acetocholinesterase blocking, and immune system stimulating bioactivities is also being developed. The supported research effort has a broad educational impact at all levels (Graduate, Undergraduate, and High School). Professor May continues to support a partnership with KIPP Sharpstown Junior High to introduce the students to experimental chemistry and other physical sciences.
This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.
