This award is funded under the American Recovery and Reinvestment Act of 2009 (Public Law 111-5). In this RUI project funded by the Inorganic, Bioinorganic, and Organometallic Chemistry Program of the Chemistry Division, Joseph Tanski of Vassar College will develop improved methods for stereoselective methylation using matched sets of chiral ligands in a catalytic system (double diastereoselectivity). Three classes of chiral chelating ligands will be synthesized, and their complexes with homoleptic titanium, scandium or ytterbium chiral alkoxides will be prepared and characterized. These complexes will then be screened in methylations of aldehydes, and structure-activity relationships will be developed. This research will impact the field of asymmetric catalysis, which is important in the chemical synthesis and pharmaceutical industries. This project also will impact the education of undergraduate students by exposing them to the field of asymmetric catalysis and by providing them with training in structure determination using X-ray diffraction methods.