U.S.-France Cooperative Research: Optically Pure Ortho-Quinone Methide Complexes- Synthesis and Stereoselective C-C Bond Formation

San Diego State University Foundation, San Diego CA

Investigators

Abstract

0128861 Grotjahn This three-year award for US-France collaboration in organometallic chemistry involves researchers and students at the San Diego State University and University Pierre and Marie Curie (Paris VI). Douglas B. Grotjahn in the US and Hani Amouri in France lead further investigations of stable metal complexes - simple ortho quinone methides (o-QMs) - discovered recently by the Amouri team. In the absence of metal, o-QMs are capable of forming complex organic molecules or damaging DNA. The Amouri-Grotjahn collaboration will use metals to stabilize the o-QM by binding tightly to it. Preliminary studies show reactivity of o-QM complexes with the metal iridium. Complexes of other metals are expected to show different reactivity. The investigators will use coordinated o-QM ligands to create new carbon-carbon bonds and rings. Optically pure samples of o-QM complexes will be used to make single enantiomers (mirror images) of the products. The US investigator brings to this collaboration expertise in optically active organic molecules and synthetic application of organic cycloadditions using advanced Nuclear Magnetic Resonance (NMR) techniques. This is complemented by French expertise in the chemistry of quinone methide complexes and their application. The collaboration advances understanding of o-QM complexes and their synthetic applications in products. Students from a predominantly undergraduate research institution will gain international experience and benefit from training in new synthetic techniques used in the French laboratory. This award represents the US side of parallel proposals to the NSF and the CNRS. NSF will cover travel funds and living expenses for the US investigator and students. The CNRS will support visits by French researchers and students to the United States.